Triethylamine → HCID 15896222, compound

HRID 1872279Notes

Reaction equation

HRID 1872279 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1.[NH2:15][C:16]1[CH:17]=[C:18]([C:22]2[C:26]([Br:27])=[CH:25][N:24]([CH3:28])[N:23]=2)[CH:19]=[CH:20][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:27][C:26]1[C:22]([C:18]2[CH:17]=[C:16]([NH:15][C:8]([C:7]3[CH:11]=[CH:12][C:4]([O:3][C:2]([F:14])([F:13])[F:1])=[CH:5][CH:6]=3)=[O:9])[CH:21]=[CH:20][CH:19]=2)=[N:23][N:24]([CH3:28])[CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 27353913-(4-Bromo-1-Methyl-1H-Pyrazol-3-Yl)Aniline

Product 1

HCID 15896222HCID 15896222, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-(trifluoromethoxy)benzoyl chloride (19 μL, 0.12 mmol) in CH2Cl2 (1 mL) was added dropwise a solution of 3-(3-aminophenyl)-4-bromo-1-methylpyrazole (30 mg, 0.12 mmol) and triethylamine (17 μL, 0.12 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 (40 mg, 76%), m.p. 138.6-139.6° C. (EtOAc/hexane).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-fa8a05cf3af648b3a6b6d74122d35254
Source dataset
uspto-grants-2000_08
Patent number
US06107324

Reaction notes

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