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Triethylamine → ethyl 4,4-difluoro-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate

HRID 1748294
Notes
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Reaction equation

HRID 1748294 reaction equation
[NH2:1][CH2:2][C:3]([F:25])([F:24])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=2)[CH:7]=[C:6]1[C:19](OCC)=[O:20].C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C(O)C>[F:24][C:3]1([F:25])[CH2:4][N:5]2[C:13]3[CH:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:9][C:8]=3[CH:7]=[C:6]2[C:19](=[O:20])[NH:1][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 67235788diethyl 1-(3-amino-2,2-difluoropropyl)-1H-indole-2,6-dicarboxylate

Product 1

HCID 67235837ethyl 4,4-difluoro-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of diethyl 1-(3-amino-2,2-difluoropropyl)-1H-indole-2,6-dicarboxylate (2.3 g) in ethanol (160 mL) are added triethylamine (2.7 mL, 19.0 mmol) and K2CO3 (1.3 g, 9.5 mmol). The mixture is heated at 80° C. for 16 h. Ethanol is removed under vacuum and water (100 mL) is added. The resulting light yellow solid is filtered and dried to afford the title compound (1.2 g, 70% for 3 steps).

Workup

  1. customEthanol is removed under vacuum and water (100 mL)
  2. additionis added
  3. filtrationThe resulting light yellow solid is filtered
  4. customdried

Sources & evidence

ORD record
ord-53a90e529eb14dd1abcc102a91bb120b
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150577B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes