4-Fluorobenzamide → 7-(4-Fluoro-benzoylamino)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

HRID 1481129Notes

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](Br)[CH:10]=2)=[O:5])[CH3:2].[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:20]=1>>[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]([NH:25][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][C:19]([F:18])=[CH:20][CH:21]=1)[CH:10]=2)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 715724-Fluorobenzamide

HCID 89813095Ethyl 7-bromo-4-hydroxyisoquinoline-3-carboxylate

Product 1

HCID 898129887-(4-Fluoro-benzoylamino)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

Procedure

7-(4-Fluoro-benzoylamino)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester was prepared from 7-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester under conditions analogous to Example 116(a) using 4-Fluorobenzamide. 1H NMR (200 MHz, CDCl3): δ ppm=11.87 (s, 1H), 8.79 (s, 1H), 8.58 (s, 1H), 8.36 (d, 1H), 8.12 (br s, 1H), 7.95 (m, 2H), 7.74 (d, 1H), 7.15-7.24 (m, 3H), 4.56 (q, 2H), 1.51 (t, 3H.)

Sources & evidence

ORD record: ord-d5e4236a55a7432c928fe5cd8c8efa14
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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