Acetic Acid → 4,4-difluoro-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid

HRID 1748295Notes

Reaction equation

HRID 1748295 reaction equation
[F:1][C:2]1([F:22])[CH2:20][N:7]2[C:8]3[CH:9]=[C:10]([C:15]([O:17]CC)=[O:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:21])[NH:4][CH2:3]1.[OH-].[Na+].C(O)(=O)C.O>C(O)C>[F:22][C:2]1([F:1])[CH2:20][N:7]2[C:8]3[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:21])[NH:4][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67235837ethyl 4,4-difluoro-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate

Product 1

HCID 672361994,4-difluoro-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acidYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4,4-difluoro-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate (470 mg, 1.5 mmol) is suspended in ethanol (17 mL) and 1M NaOH solution (4.8 mL, 4.8 mmol) is added. The reaction mixture is heated at 60° C. for 1 h 50 min. Acetic acid (15 mL) and water (100 mL) are added and the resulting white solid is filtered and rinsed with water to afford the title compound (350 mg, 82%).

Workup

  1. filtrationthe resulting white solid is filtered
  2. washrinsed with water

Sources & evidence

ORD record
ord-64c12f4113cd4e8ea1ee1d9c49f4e12b
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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