HCID 23717243, compound → HCID 67085605, compound

HRID 2036702Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9]([O-:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[Na+].Br[C:14]1[CH:22]=[CH:21][C:20]2[N:19]([CH3:23])[C:18]3[CH2:24][CH:25]4[NH:29][CH:28]([C:17]=3[C:16]=2[C:15]=1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][CH2:26]4>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9]([C:14]2[CH:22]=[CH:21][C:20]3[N:19]([CH3:23])[C:18]4[CH2:24][CH:25]5[NH:29][CH:28]([C:17]=4[C:16]=3[C:15]=2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][CH2:26]5)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 23717243HCID 23717243, compound

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

Product 1

HCID 67085605HCID 67085605, compoundYield 63%

Procedure

Intermediate 7 was coupled with the product of Example 27, step B following the procedure of Example 27, step C. The crude product was purified by flash column chromatography (SiO2, 7:3 hexanes/ethyl acetate) to give tert-butyl 2-(3-methoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (194 mg, 63%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 8.19 (s, 1H), 7.67 (d, J=8.1 Hz, 1H), 7.47-7.52 (m, 2H), 7.26-7.37 (m, 2H), 6.98-7.08 (m, 1H), 5.25-5.29 (m, 1H), 4.70 (br s, 1H), 3.82 (s, 3H), 3.60 (s, 3H), 3.36-3.49 (m, 1H), 2.49 (d, J=16.0 Hz, 1H), 2.25-2.33 (m, 1H), 2.16-2.23 (m, 1H), 1.90-1.97 (m, 1H), 1.50-1.70 (m, 1H), 1.37 (s, 9H).

Workup

customThe crude product was purified by flash column chromatography (SiO2, 7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-0730476ac5324f2da95f12e20a429025
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

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