Glycine → {[2,3-Dibromo-1-(4-fluoro-benzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carbonyl]-amino}-acetic acid

HRID 642445Notes

Reaction equation

C(O[C:4]([C:6]1[C:7]([OH:25])=[C:8]2[C:14]([Br:15])=[C:13]([Br:16])[N:12]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])C.[NH2:26][CH2:27][C:28]([OH:30])=[O:29].C[O-].[Na+].CO>>[Br:16][C:13]1[N:12]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:9]2=[CH:10][N:11]=[C:6]([C:4]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:5])[C:7]([OH:25])=[C:8]2[C:14]=1[Br:15]

Participants

Reactant 3

HCID 750Glycine

HCID 23694274Sodium methanolate methanol

HCID 598558191h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,2,3-dibromo-1-[(4-fluorophenyl)methyl]-4-hydroxy-,ethyl ester

Product 1

HCID 68426433{[2,3-Dibromo-1-(4-fluoro-benzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carbonyl]-amino}-acetic acid

Procedure

Prepared in analogy to that of Example 1(e) from 2,3-dibromo-1-(4-fluoro-benzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester, glycine and NaOMe/HOMe. The title compound, ESI MS (m/z): 500 (M+H)+.

Sources & evidence

ORD record: ord-ed0c390361a3431fa4b37ba48def3a03
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696223B2

Reaction notes

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