N-bromobutanimide → 1-Bromo-7-(2,6-difluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

HRID 1480964Notes

Reaction equation

HRID 1480964 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=1[F:25])[CH:10]=2)=[O:5])[CH3:2].C1C(=O)N([Br:33])C(=O)C1>CC#N>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:33])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=1[F:25])[CH:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 898130217-(2,6-Difluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 898129771-Bromo-7-(2,6-difluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl esterYield 60.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7-(2,6-difluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester (210 mg) and NBS (133 mg) in MeCN (5 mL) was stirred in an ice/water bath for 2 h; then concentrated, the residue was column purified to give the desired product (156 mg). LC MS ESI: 424 (M+1)+.

Workup

  1. concentrationthen concentrated
  2. custompurified

Sources & evidence

ORD record
ord-1f82058e59c24734a6a9642ce4faf995
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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