Acetic Anhydride → 7-(acetamidomethyl)-4-bromo-9H-carbazole-1-carboxamide

HRID 661939Notes

Reaction equation

HRID 661939 reaction equation
[NH2:1][CH2:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:8]([Br:19])=[CH:9][CH:10]=[C:11]([C:16]([NH2:18])=[O:17])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C1COCC1>[C:20]([NH:1][CH2:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:8]([Br:19])=[CH:9][CH:10]=[C:11]([C:16]([NH2:18])=[O:17])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 666063397-(aminomethyl)-4-bromo-9H-carbazole-1-carboxamide

Product 1

HCID 666065877-(acetamidomethyl)-4-bromo-9H-carbazole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 1 A suspension of 7-(aminomethyl)-4-bromo-9H-carbazole-1-carboxamide (prepared according to Step 2 of Example 33-1, 168 mg, 0.528 mmol) and TEA (0.184 mL, 1.320 mmol) in THF (18 mL) was treated with acetic anhydride (0.080 mL, 0.845 mmol). The mixture was stirred at rt for 2 h, then was partitioned between EtOAc and 1 M hydrochloric acid. The organic phase was washed with NaHCO3 (aq) and brine, dried and concentrated to provide 7-(acetamidomethyl)-4-bromo-9H-carbazole-1-carboxamide as an off-white solid. Mass spectrum m/z 359.9 (M+H)+.

Workup

  1. customwas partitioned between EtOAc and 1 M hydrochloric acid
  2. washThe organic phase was washed with NaHCO3 (aq) and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8b8ad118c581487f92adac5a347147c5
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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