Benzyl chloroformate → HCID 70226091, compound

HRID 1531550Notes

Reaction equation

HRID 1531550 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].C(N(C(C)C)CC)(C)C.[CH3:21][C:22]1[CH:23]=[C:24]([C:29]2[NH:30][C:31]3[C:36]([CH:37]=2)=[CH:35][C:34]([NH2:38])=[CH:33][CH:32]=3)[CH:25]=[C:26]([CH3:28])[CH:27]=1>>[CH2:5]([O:4][C:2](=[O:3])[NH:38][C:34]1[CH:35]=[C:36]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([C:24]1[CH:23]=[C:22]([CH3:21])[CH:27]=[C:26]([CH3:28])[CH:25]=1)=[CH:37]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 212541012-(3,5-Dimethylphenyl)-1H-indol-5-amine

Product 1

HCID 70226091HCID 70226091, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3,5-dimethylphenyl)-5-amino-1H-indole (1.16 g in 60 mL dry methylene chloride) at −60 ° C. was added 0.86 mL benzyl chloroformate followed by 1 mL diisopropylethylamine and the mixture warmed slowly to 0° C. After 45 minutes, the reaction was quenched by the addition of saturated aqueous ammonium chloride and the mixture extracted with methylene chloride. The organic portion was washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography (hexane:methylene chloride:ethyl acetate, 8:8:1; then 7:7:1) gave the title compound (1.68 g).

Workup

  1. customthe reaction was quenched by the addition of saturated aqueous ammonium chloride
  2. extractionthe mixture extracted with methylene chloride
  3. washThe organic portion was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (hexane

Sources & evidence

ORD record
ord-8612b79a90164243839f49b48a763104
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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