4-(Trifluoromethyl)benzaldehyde → 4-Bromo-1-[(4-trifluoromethyl-benzylidene)-amino]-1H-pyrrole-2-carboxylic acid methyl ester

HRID 1511991Notes

Reaction equation

HRID 1511991 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([NH2:11])[CH:7]=[C:8]([Br:10])[CH:9]=1)=[O:4].[F:12][C:13]([F:23])([F:22])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1>>[CH3:1][O:2][C:3]([C:5]1[N:6]([N:11]=[CH:18][C:17]2[CH:16]=[CH:15][C:14]([C:13]([F:12])([F:22])[F:23])=[CH:21][CH:20]=2)[CH:7]=[C:8]([Br:10])[CH:9]=1)=[O:4]

Participants

3

Reactant 2

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 58423493Methyl 1-amino-4-bromo-1H-pyrrole-2-carboxylate

Product 1

HCID 672321444-Bromo-1-[(4-trifluoromethyl-benzylidene)-amino]-1H-pyrrole-2-carboxylic acid methyl ester

Procedure

Prepared according to the imine formation condition used in Example 18 step b) from 1-amino-4-bromo-1H-pyrrole-2-carboxylic acid methyl ester and 4-trifluoromethylbenzaldehyde. 1H NMR (CDCl3, δ in ppm): 8.44 (s, 1H), 7.96 (d, 2H, J=7.8 Hz), 7.70 (d, 2H, J=7.8 Hz), 7.27 (d, 1H, J=1.8 Hz), 6.99 (d, 1H, J=1.6 Hz), 3.85 (s, 3H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-e09e78dc167f44aab69af72b6030674d
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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