HCID 58258876, compound → HCID 67085203, compound

HRID 2036724Notes

Reaction equation

HRID 2036724 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([S:6]([O-:8])=[O:7])=[CH:2]1.[Na+].Br[C:11]1[CH:19]=[CH:18][C:17]2[N:16]([CH3:20])[C:15]3[CH2:21][CH:22]4[NH:26][CH:25]([C:14]=3[C:13]=2[C:12]=1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24][CH2:23]4>>[S:1]1[CH:5]=[CH:4][C:3]([S:6]([C:11]2[CH:19]=[CH:18][C:17]3[N:16]([CH3:20])[C:15]4[CH2:21][CH:22]5[NH:26][CH:25]([C:14]=4[C:13]=3[C:12]=2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24][CH2:23]5)(=[O:8])=[O:7])=[CH:2]1

Participants

3

Reactant 2

HCID 58258876HCID 58258876, compoundHCID 67085938Tert-butyl 2-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67085203HCID 67085203, compoundYield 31%

Procedure

Intermediate 25 was coupled with the product of Example 27, step B following the procedure of Example 27, step C. The crude material was purified by flash column chromatography (SiO2, hexane/ethyl acetate 55:45) to give tert-butyl 2-(3-thienyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (130 mg, 31%) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.20 (s, 1H), 8.02-8.53 (m, 1H), 7.66-7.74 (m, 1H), 7.28-7.37 (m, 3H), 5.26 (br s, 1H), 4.70 (br s, 1H), 3.61 (s, 3H), 3.38 (br s, 1H), 2.50 (d, J=15.9 Hz, 1H), 2.12-2.41 (m, 2H), 1.89-2.00 (m, 1H), 1.57-1.68 (m, 1H), 1.48 (s, 9H).

Workup

  1. customThe crude material was purified by flash column chromatography (SiO2, hexane/ethyl acetate 55:45)

Sources & evidence

ORD record
ord-405b87948d2946289b19791f85e070e9
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

Loading…