15898-46-1 → HCID 67085522, compound

HRID 2036706Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([O-:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Na+].Br[C:15]1[CH:23]=[CH:22][C:21]2[N:20]([CH3:24])[C:19]3[CH2:25][CH:26]4[NH:30][CH:29]([C:18]=3[C:17]=2[C:16]=1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:28][CH2:27]4>>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([C:15]2[CH:23]=[CH:22][C:21]3[N:20]([CH3:24])[C:19]4[CH2:25][CH:26]5[NH:30][CH:29]([C:18]=4[C:17]=3[C:16]=2[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:28][CH2:27]5)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 1136779315898-46-1

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

Product 1

HCID 67085522HCID 67085522, compoundYield 13%

Procedure

Intermediate 8 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, 3:2 hexane/ethyl acetate) to give tert-butyl 2-(3-nitrophenylsulfonyl)-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (50 mg, 13%) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.76 (s, 1H), 8.25-8.38 (m, 1H), 8.21 (s, 1H), 7.67-7.72 (m, 2H), 7.65 (s, 1H), 7.35 d, J=8.7 Hz, 1H), 5.27 (br s, 1H) 4.70-4.73 (m, 1H), 3.62 (s, 3H), 3.38-3.42 (m, 1H), 2.51 (d, J=15 Hz, 1H), 2.15-2.42 (m, 2H), 1.97-1.90 (m, 1H), 1.54-1.67 (m, 1H), 1.37 (s, 9H).

Workup

customThe crude material was purified by flash column chromatography (SiO2, 3:2 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-f6f0ddc5dcf34f9fa2000579b659e940
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

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