2-Bromoethyl methyl ether → HCID 136352231, compound

HRID 1853281Notes

Reaction equation

HRID 1853281 reaction equation
C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)(C)(C)C.Br[CH2:29][CH2:30][O:31][CH3:32]>>[CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[C:18]([C:9]2[O:10][C:11]3[C:16]([C:7](=[N:6][OH:5])[CH:8]=2)=[CH:15][C:14]([O:17][CH2:29][CH2:30][O:31][CH3:32])=[CH:13][CH:12]=3)[N:19]=1

Participants

3

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 86673049HCID 86673049, compound

Product 1

HCID 136352231HCID 136352231, compound

Procedure

2-isoquinolin-3-yl-6-(2-methoxy-ethoxy)-chromen-4-one oxime was prepared in 67% overall yield using the method described in example 42 and 42A, starting from 6-hydroxy-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (example 41A) and bromoethylmethylether instead of iodomethane. The title compound was isolated as a yellow solid after purification by flash chromatography over silica gel (cyclohexane/ethyl acetate: 0-80%), and as a 85/15 mixture of Z/E oxime isomers.

Workup

  1. customoverall yield

Sources & evidence

ORD record
ord-071c6bd7f2c1432e9d074214b8b2c3c0
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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