HCID 50998759, compound → HCID 67173587, compound

HRID 2036722Notes

Reaction equation

HRID 2036722 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([O-:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=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>>[F:8][C:6]1[CH:5]=[C:4]([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:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 50998759HCID 50998759, compoundHCID 67085938Tert-butyl 2-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 67173587HCID 67173587, compoundYield 13%

Procedure

Intermediate 21 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, 8:2 hexanes/ethyl acetate) to give tert-butyl 2-(3,5-difluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (40 mg, 13%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 8.17 (s, 1H), 7.67 (d, J=8.7 Hz, 1H), 7.44-7.50 (m, 2H), 7.34 (d, J=8.7 Hz, 1H), 6.91-6.96 (m, 1H), 5.26 (br s, 1H), 4.71 (br s, 1H), 3.62 (s, 3H), 3.39 (br s, 1H), 2.48 (d, J=16.0 Hz, 1H), 2.18-2.35 (m, 2H), 1.91-1.99 (m, 1H), 1.50-1.68 (m, 1H), 1.37 (s, 9H)

Workup

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

Sources & evidence

ORD record
ord-07709a4baa1447d68279982163e40b12
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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