Ammonia → 9-bromo-8-fluoro-5,6-dihydro-4H-4,6-methanobenzo[3,4]cyclohepta[1,2-b]thiophene-2-carboxamide

HRID 575452Notes

Reaction equation

HRID 575452 reaction equation
[Br:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[CH:19]3[CH2:20][CH:17]([CH2:18]3)[C:8]3[S:9][C:10]([C:12](OCC)=[O:13])=[CH:11][C:7]=3[C:6]=2[CH:21]=1.[NH3:23]>>[Br:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[CH:19]3[CH2:20][CH:17]([CH2:18]3)[C:8]3[S:9][C:10]([C:12]([NH2:23])=[O:13])=[CH:11][C:7]=3[C:6]=2[CH:21]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86693514ethyl 9-bromo-8-fluoro-5,6-dihydro-4H-4,6-methanobenzo[3,4]cyclohepta[1,2-b]thiophene-2-carboxylate

Product 1

HCID 866935159-bromo-8-fluoro-5,6-dihydro-4H-4,6-methanobenzo[3,4]cyclohepta[1,2-b]thiophene-2-carboxamideYield 100%

Conditions

Temperature
45 °C

Procedure

A pressure tube containing a solution of ethyl 9-bromo-8-fluoro-5,6-dihydro-4H-4,6-methanobenzo[3,4]cyclohepta[1,2-b]thiophene-2-carboxylate (32 mg, 0.08 mmol) in methanolic ammonia (5 mL of 7.0M ammonia in methanol) was warmed to 45° C. for two weeks. Evaporation of the reaction mixture furnished the title compound (31 mg, 0.08 mmol, 100%) as a pale brown solid: 1H NMR (500 MHz, d4-methanol) delta 1.61-1.68 (m, 2H), 2.93-3.02 (m, 2H), 3.59 (td, J=7.33, 4.26 Hz, 1H), 3.67 (td, J=8.04, 3.78 Hz, 1H), 7.05 (d, J=9.46 Hz, 1H), 8.18 (d, J=6.94 Hz, 1H), 8.39 (s, 1H); M+1=352/354.

Workup

  1. customEvaporation of the reaction mixture

Sources & evidence

ORD record
ord-07924eed96774cef93c8241904d1b34e
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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