Diphenyl sulfone → HCID 67085359, compound

HRID 2036738Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]([F: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]([F: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 67085400HCID 67085400, compound

Product 1

HCID 67085359HCID 67085359, compoundYield 26%

Procedure

The product of step C 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 hexane/ethyl acetate) to give tert-butyl 2-phenylsulfonyl-4-fluoro-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (61 mg, 26%) as an off-white solid: 1H NMR (CDCl3, 300 MHz): δ 7.91-7.99 (m, 3H), 7.43-7.55 (m, 3H), 7.28-7.36 (m, 1H), 5.13-5.31 (m, 1H), 4.58-4.70 (m, 1H), 3.78 (s, 3H), 3.14-3.50 (m, 1H), 2.41 (d, J=19.2 Hz, 1H), 2.12-2.40 (m, 2H), 1.86-1.97 (m, 1H), 1.58-1.68 (m, 1H), 1.38 (br s, 9H).

Workup

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

Sources & evidence

ORD record: ord-62767852b1a94278a6e59c7cc688edb4
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

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