Benzenesulfinic acid, sodium salt → HCID 68109053, compound

HRID 2179362Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[O:15][C:14]3[CH2:13][CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:9][C:8]=3[C:6]=2[CH:7]=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:3]=[CH:4][C:5]3[O:15][C:14]4[CH2:13][CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:9][C:8]=4[C:6]=3[CH:7]=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 68108711HCID 68108711, compound

Product 1

HCID 68109053HCID 68109053, compoundYield 22%

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 9-(phenylsulfonyl)-4,5-dihydro-1H-benzofuro[3,2-c]azepine-2(3H)-carboxylate (22 mg, 22%) as a light yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.09 (br s, 1H), 8.00-7.91 (m, 2H), 7.86-7.77 (m, 1H), 7.58-7.37 (m, 4H), 4.68-4.38 (m, 2H), 3.70 (br s, 2H), 3.01 (t, J=6.0 Hz, 2H), 2.09-1.92 (m, 2H), 1.53-1.20 (m, 9H).

Workup

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

Sources & evidence

ORD record: ord-9e5b1313088246f4a410ebc35edd3007
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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