Diphenyl sulfone → HCID 67085431, compound

HRID 2036740Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]([Cl:11])[C:8]2[N:7]([CH3:12])[C:6]3[CH2:13][CH:14]4[NH:18][CH:17]([C:5]=3[C:4]=2[C:3]=1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16][CH2:15]4.[C:26]1([S:32](C2C=CC=CC=2)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:26]1([S:32]([C:2]2[CH:10]=[C:9]([Cl:11])[C:8]3[N:7]([CH3:12])[C:6]4[CH2:13][CH:14]5[NH:18][CH:17]([C:5]=4[C:4]=3[C:3]=2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16][CH2:15]5)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Reactant 2

HCID 31386Diphenyl sulfone

HCID 67085206HCID 67085206, compound

Product 1

HCID 67085431HCID 67085431, compoundYield 63%

Procedure

The product of step E was converted to the phenylsulfone derivative following the procedure of Example 71, step D. The crude product was purified by flash column chromatography (SiO2, 75:25 hexanes/ethyl acetate) to give tert-butyl 2-phenylsulfonyl-4-chloro-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (165 mg, 63%) as an off-white solid: 1H NMR (CDCl3, 300 MHz): δ 8.02-8.07 (m, 1H), 7.91-7.97 (m, 2H), 7.42-7.62 (m, 4H), 5.10-5.32 (m, 1H), 4.55-4.80 (m, 1H), 3.94 (s, 3H), 3.15-3.48 (m, 1H), 2.47 (d, J=16.2 Hz, 1H), 2.10-2.40 (m, 2H), 1.85-1.96 (m, 1H), 1.52-1.65 (m, 1H), 1.38 (br s, 9H).

Workup

customThe crude product was purified by flash column chromatography (SiO2, 75:25 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-55566e2dbfb94807ac13d7d6c055318f
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

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