m-Ethynylphenol → HCID 136352227, compound

HRID 1853272Notes

Reaction equation

C([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][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.[OH:28][C:29]1[CH:30]=[C:31]([C:35]#[CH:36])[CH:32]=[CH:33][CH:34]=1>>[OH:28][C:29]1[CH:30]=[C:31]([C:35]#[C:36][C:13]2[CH:14]=[C:15]3[C:16]([C:7](=[N:6][OH:5])[CH:8]=[C:9]([C:18]4[N:19]=[CH:20][C:21]5[C:26]([CH:27]=4)=[CH:25][CH:24]=[CH:23][CH:22]=5)[O:10]3)=[CH:11][CH:12]=2)[CH:32]=[CH:33][CH:34]=1

Participants

Reactant 2

HCID 139144m-Ethynylphenol

HCID 86673023HCID 86673023, compound

Product 1

HCID 136352227HCID 136352227, compound

Procedure

7-(3-hydroxyphenyl)ethynyl-2-isoquinolin-3-yl-chromen-4-one oxime was prepared in 28% overall yield using the method described in example 24, starting from 7-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (example 2B) and 3-hydroxyphenylacetylene. The title compound was isolated as a yellow solid and as a 80/20 mixture of Z/E oxime isomers.

Workup

customoverall yield

Sources & evidence

ORD record: ord-dc88636ad6aa42e6a7672aafe0207067
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962627B2

Reaction notes

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