Benzenesulfinic acid, sodium salt → HCID 67085715, compound

HRID 2036756Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][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]([O-:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Na+]>>[C:26]1([S:32]([C:2]2[CH:10]=[CH:9][C:8]3[N:7]([CH2:11][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 2723840Benzenesulfinic acid, sodium salt

HCID 67085719HCID 67085719, compound

Product 1

HCID 67085715HCID 67085715, compoundYield 36%

Procedure

The product of step A was coupled with sodium benzenesulfinate following the procedure of Example 27, step C. The crude material was purified by flash column chromatography (SiO2, 4:1 to 1:1 hexane/ethyl acetate) to give tert-butyl 2-phenylsulfonyl-5-ethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (0.12 g, 36%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.20 (s, 1H), 7.94-7.99 (m, 2H), 7.40-7.53 (m, 4H), 7.31 (d, J=8.7 Hz, 1H), 5.20-5.33 (m, 1H), 4.55-4.81 (m, 1H), 3.95-4.11 (m, 2H), 3.19-3.50 (m, 1H), 2.47 (d, J=16.2 Hz, 1H), 2.15-2.38 (m, 2H), 1.91-2.01 (m, 1H), 1.53-1.62 (m, 1H), 1.34 (s, 9H), 1.25-1.31 (m, 3H).

Workup

customThe crude material was purified by flash column chromatography (SiO2, 4:1 to 1:1 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-f7a6a550d52a4b6eb760f2a898ad98cd
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

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