Triethylamine → HCID 9841895, compound

HRID 1761300Notes

Reaction equation

HRID 1761300 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[NH2:9][C:10]1[CH:11]=[C:12]([C:16]2[C:20]([Br:21])=[CH:19][N:18]([CH3:22])[N:17]=2)[CH:13]=[CH:14][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:21][C:20]1[C:16]([C:12]2[CH:11]=[C:10]([NH:9][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[O:7])[CH:15]=[CH:14][CH:13]=2)=[N:17][N:18]([CH3:22])[CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 27353913-(4-Bromo-1-Methyl-1H-Pyrazol-3-Yl)Aniline

Product 1

HCID 9841895HCID 9841895, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To thiophene-2-carbonyl chloride (11 μL, 0.09 mmol) in CH2Cl2 (1 mL) was added dropwise a solution of 3-(3-aminophenyl)-4-bromo-1-methylpyrazole (25 mg. 0.09 mmol) and triethylamine (14 μL, 0.09 mmol) in CH2Cl2 (0.5 mL). The reaction mixture was stirred for 16 h and concentrated. Chromatography on flash silica (50% EtOAc/hexane) gave the title compound as a colourless solid (24 mg, 68%), m.p. 127.8-128.6° C. (EtOAc/hexane).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-966c14b5a49f4b4dbdd229b59a1c2e83
Source dataset
uspto-grants-2005_01
Patent number
US06846919B2

Reaction notes

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