Trityl chloride → N-(5-(3,5-Difluorobenzoyl)-1-trityl-1H-indazol-3-yl)-2,2,2-trifluoroacetamide

HRID 571891Notes

Reaction equation

HRID 571891 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[C:24]([F:26])[CH:25]=1)[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])=[O:6].Cl[C:28]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[C:24]([F:26])[CH:25]=1)[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:28]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[N:11]=[C:10]2[NH:16][C:17](=[O:22])[C:18]([F:20])([F:21])[F:19])=[O:6]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 86647613N-(5-(3,5-Difluorobenzoyl)-1H-indazol-3-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 86647614N-(5-(3,5-Difluorobenzoyl)-1-trityl-1H-indazol-3-yl)-2,2,2-trifluoroacetamideYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[5-(3,5-Difluoro-benzoyl)-1H-indazol-3-yl]-2,2,2-trifluoro-acetamide (19.11 g, 51.76 mmol) in dry dichloromethane (300 mL) was treated with chlorotriphenylmethane (14.72 g, 52.8 mmol) and triethylamine (14.55 mL, 103.5 mmol). After stirring at room temperature for two days, the reaction was washed with a solution of NH4Cl, dried and evaporated. Purification of the crude by chromatography over silica gel (DCM/MeOH) afforded 27.32 g of the title compound (86% yield).

Workup

  1. washthe reaction was washed with a solution of NH4Cl
  2. customdried
  3. customevaporated
  4. customPurification of the crude by chromatography over silica gel (DCM/MeOH)

Sources & evidence

ORD record
ord-52cca342fa76483eac7b8413572f8d16
Source dataset
uspto-grants-2015_05
Patent number
US09029356B2

Reaction notes

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