Cyclopropyloxy and other abnormal RHS para-ethers

[MFernflower]

Most all of the S4 drugs appear to use para OCHF2 or OCHF3 or sometimes methoxy - My molecule proposal is to explore variations in the para ether substitution - the needed core can be made via coupling of para-hydroxyphenylbornic acid (THP-protected is also commercially available) to the LHS furnished core that @maratsydney has been working with for quite sometime now - followed by normal Williamson ether conditions with desired halogenated precursor

I understand these compounds are going to be oily but this is a portion of SAR I feel we have never ever explored

SMILES STRINGS:
OC1=CC=C(C=C1)C1=NN=C2C=NC=C(OCCC3=CC=CC=C3)N12
CC(C)OC1=CC=C(C=C1)C1=NN=C2C=NC=C(OCCC3=CC=CC=C3)N12
C(CC1=CC=CC=C1)OC1=CN=CC2=NN=C(N12)C1=CC=C(OC2CC2)C=C1
CN(C)S(=O)(=O)OC1=CC=C(C=C1)C1=NN=C2C=NC=C(OCCC3=CC=CC=C3)N12
CCOC1=CC=C(C=C1)C1=NN=C2C=NC=C(OCCC3=CC=CC=C3)N12

Reagent prices:
Isopropyl chloride/bromide - common lab chemical
Ethyl bromide - common lab chemical
Required boronic acid: 84 AUD from sigma (1 gram package) (Sigma catalogue number 523976)
Cyclopropyl bromide: 74 AUD from sigma (5 gram package) - Might already have at lab?
Sulfamate precursor: - Sigma only sells package of 100 grams so need to find other source