Acetyl bromide → HCID 58203527, compound

HRID 2194778Notes

Reaction equation

HRID 2194778 reaction equation
C(Br)(C)=O.[CH3:5][C:6]1[CH:7]=[C:8]([C:28]#[N:29])[C:9]2[CH:10]=[CH:11][N:12]([C:15]3[C:20]([CH:21]([CH3:23])[CH3:22])=[C:19]([O:24]C)[N:18]=[C:17]([O:26]C)[N:16]=3)[C:13]=2[CH:14]=1>>[CH:21]([C:20]1[C:19](=[O:24])[NH:18][C:17](=[O:26])[NH:16][C:15]=1[N:12]1[C:13]2[CH:14]=[C:6]([CH3:5])[CH:7]=[C:8]([C:28]#[N:29])[C:9]=2[CH:10]=[CH:11]1)([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 10482Acetyl bromideHCID 58203502HCID 58203502, compound

Product 1

HCID 58203527HCID 58203527, compoundYield 65%

Conditions

Temperature
70 °C

Procedure

AcBr (3 mL) was added to 6-methyl-1-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-1H-indole-4-carbonitrile (470 mg, 1.40 mmol). The reaction mixture was heated at 70° C. for 6 hours. The reaction mixture was then cooled to room temperature and concentrated. The crude reaction product was purified (silica gel, 0-80% EtOAc/hexane) to give a white solid (280 mg, 65%). LC-MS shows 307.1 (M−1).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated
  3. customThe crude reaction product
  4. customwas purified (silica gel, 0-80% EtOAc/hexane)

Sources & evidence

ORD record
ord-91b4b5ca05e1467e81ea0b6df9e6c140
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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