HCID 23675619, compound → HCID 67085645, compound

HRID 2036711Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([O-:13])=[O:12].[Na+].Br[C:16]1[CH:24]=[CH:23][C:22]2[N:21]([CH3:25])[C:20]3[CH2:26][CH:27]4[NH:31][CH:30]([C:19]=3[C:18]=2[C:17]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][CH2:28]4>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([C:16]1[CH:24]=[CH:23][C:22]2[N:21]([CH3:25])[C:20]3[CH2:26][CH:27]4[NH:31][CH:30]([C:19]=3[C:18]=2[C:17]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][CH2:28]4)(=[O:13])=[O:12]

Participants

Reactant 2

HCID 23675619HCID 23675619, compound

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

Product 1

HCID 67085645HCID 67085645, compoundYield 24%

Procedure

Intermediate 24 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, 8:2 hexanes/ethyl acetate) to give tert-butyl 2-(2-napthyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (113 mg, 24%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.58 (d, J=0.9 Hz, 1H), 8.26 (s, 1H), 7.93-8.04 (m, 1H), 7.81-7.88 (m, 2H), 7.71 (d, J=9.9 Hz, 1H), 7.52-7.63 (m, 2H), 7.42-7.51 (m, 1H), 7.29 (d, J=8.7 Hz, 1H), 5.26 (br s, 1H), 4.71 (br s, 1H), 3.59 (s, 3H), 3.39 (br s, 1H), 2.49 (d, J=16.2 Hz, 1H), 2.20-2.48 (m, 2H), 1.88-1.99 (m, 1H), 1.59-1.67 (m, 1H), 1.37 (br s, 9H).

Workup

customThe crude material was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-2c372434eba6412e936783029aa327a6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

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