Acetyl chloride → HCID 21964303, compound

HRID 1791496Notes

Reaction equation

HRID 1791496 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1[CH:34]=[CH:33][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]4[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=4)=[CH:17][CH:18]=3)[CH:13]=[C:12]2[CH2:31][OH:32])=[CH:8][CH:7]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]([O:32][CH2:31][C:12]1[N:11]([CH2:10][C:9]2[CH:8]=[CH:7][C:6]([CH3:5])=[CH:34][CH:33]=2)[C:19]2[C:14]([CH:13]=1)=[CH:15][C:16]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:29])([F:30])[F:28])=[CH:22][CH:21]=1)=[CH:17][CH:18]=2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 21964288HCID 21964288, compound

Product 1

HCID 21964303HCID 21964303, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.222 mL, 3.08 mmol) was added to a stirring solution of {1-(4-methylbenzyl)-5-[4-(trifluoromethoxy)phenyl]-1H-indol-2-yl}methanol (0.507 g, 1.23 mmol) and N,N-diisopropylethylamine (0.547 mL, 3.08 mmol) in methylene chloride (8 mL) at 0° C. under a nitrogen atmosphere over a period of 5 minutes. After the reaction mixture was stirred at room temperature overnight, the reaction quenched carefully with water. The aqueous mixture was extracted with ethyl acetate. The organic extract was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated to afford the title compound as a solid (0.557 g, 99.6%), mp: 125-126° C. Mass spectrum (ESI, [M+H]+) m/z 454. 1HNMR (400 MHz, DMSO-d6): δ 7.86 (s, 1H), 8.77 (d, 2H, J=8.96 Hz), 7.48-7.40 (m, 4H), 7.09 (d, 2H, J=7.94 Hz), 6.90 (d, 2H, J=7.94 Hz), 6.70 (s, 1H), 5.44 (s, 2H), 5.23 (s, 2H), 2.23 (s, 3H), and 1.85 ppm (s, 3H).

Workup

  1. customthe reaction quenched carefully with water
  2. extractionThe aqueous mixture was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-80d80c1c55fb4578bdb49d8fb3a9d1a5
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Reaction notes

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