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

HRID 1748294Notes

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

Participants

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

customEthanol is removed under vacuum and water (100 mL)
additionis added
filtrationThe resulting light yellow solid is filtered
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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