Triethylamine → HCID 15896223, compound

HRID 2355812Notes

Reaction equation

HRID 2355812 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([C:18]2[C:22]([Br:23])=[CH:21][N:20]([CH3:24])[N:19]=2)[CH:15]=[CH:16][CH:17]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:23][C:22]1[C:18]([C:14]2[CH:13]=[C:12]([NH:11][C:6]([C:5]3[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:7])[CH:17]=[CH:16][CH:15]=2)=[N:19][N:20]([CH3:24])[CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 27353913-(4-Bromo-1-Methyl-1H-Pyrazol-3-Yl)Aniline

Product 1

HCID 15896223HCID 15896223, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-chlorobenzoyl chloride (15 mg, 0.08 mmol) in CH2Cl2 (1 mL) was added dropwise a solution of 3-(3-aminophenyl)-4-bromo-1-methylpyrazole (21 mg, 0.08 mmol) and triethylamine (12 μL, 0.08 mmol) in CH2Cl2 (0.5 mL). The mixture was stirred for 16 h and concentrated. Chromatography on flash silica (50% EtOAc/hexane) gave the title compound as a colourless solid (23 mg, 72%), m.p. 184.4-184.8° C. (EtOAc/hexane).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-993a34dfd0a14d0c96975b30e4cb1b49
Source dataset
uspto-grants-2010_07
Patent number
US07754866B2

Reaction notes

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