Benzenesulfinic acid, sodium salt → HCID 68108906, compound

HRID 2179360Notes

Reaction equation

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

Participants

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium salt

HCID 68108869HCID 68108869, compound

Product 1

HCID 68108906HCID 68108906, compoundYield 34%

Procedure

The product of step E was coupled with sodium benzenesulfinate following the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 70:30 hexanes/ethyl acetate) provided tert-butyl 8-(phenylsulfonyl)-4,5-dihydro-1H-benzofuro[3,2-c]azepine-2(3H)-carboxylate (106 mg, 34%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.04-7.87 (m, 3H), 7.83-7.72 (m, 1H), 7.60-7.41 (m, 4H), 4.64-4.61 (m, 2H), 3.67 (br s, 2H), 3.03 (t, J=6.3 Hz, 2H), 1.99 (br s, 2H), 1.53-1.25 (m, 9H).

Workup

customPurification by flash column chromatography (SiO2, 70:30 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-ce3d1d4794af4f19bada44c7ade9b4e4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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