Diphenyl sulfone → HCID 131731027, compound

HRID 2036749Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]3[CH2:19][CH:20]4[NH:24][CH:23]([C:5]=3[C:4]=2[C:3]=1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:21]4.[C:32]1([S:38](C2C=CC=CC=2)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[C:32]1([S:38]([C:2]2[CH:10]=[CH:9][C:8]3[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]4[CH2:19][CH:20]5[NH:24][CH:23]([C:5]=4[C:4]=3[C:3]=2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:21]5)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Reactant 2

HCID 31386Diphenyl sulfone

HCID 131731028HCID 131731028, compound

Product 1

HCID 131731027HCID 131731027, compoundYield 58%

Procedure

The product of step A was converted to the phenyl sulfone derivative following the procedure of example 1, step C. The crude material was purified by flash column chromatography (SiO2 98:2 to 65:35 hexane/ethyl acetate) to give tert-butyl 2-phenylsulfonyl-5-[(trimethylsilyl)ethoxy]methyl-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole-carboxylate (1.30 g, 58%) as a brown foam: 1H NMR (CDCl3, 300 MHz) δ 8.28 (s, 1H), 8.03-8.09 (m, 2H), 7.75-7.83 (m, 1H), 7.51-7.62 (m, 4H), 5.28-5.49 (m, 3H), 4.66-4.89 (m, 1H), 3.45-3.68 (m, 3H), 2.64 (d, J=16.2 Hz, 1H), 2.45-2.52 (m, 1H), 2.25-2.38 (m, 1H), 2.01-2.11 (m, 1H), 1.64-1.75 (m, 1H), 1.46 (br s, 9H), 0.88-0.95 (m, 2H), −0.11 (s, 9H).

Workup

customThe crude material was purified by flash column chromatography (SiO2 98:2 to 65:35 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-620b3d487d59455782e9b232e4229b91
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

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