Benzenesulfinic acid, sodium salt → ethyl 7-chloro-9-(phenylsulfonyl)-4,5-dihydro-1H-benzofuro[2,3-d]azepine-3(2H)-carboxylate

HRID 2179431Notes

Reaction equation

HRID 2179431 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:21])[C:5]2[O:20][C:9]3[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14][C:8]=3[C:6]=2[CH:7]=1.[C:22]1([S:28]([O-:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Na+]>>[Cl:21][C:4]1[C:5]2[O:20][C:9]3[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14][C:8]=3[C:6]=2[CH:7]=[C:2]([S:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:30])=[O:29])[CH:3]=1

Participants

3

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium saltHCID 68109096ethyl 9-bromo-7-chloro-4,5-dihydro-1H-benzofuro[2,3-d]azepine-3(2H)-carboxylate

Product 1

HCID 68109708ethyl 7-chloro-9-(phenylsulfonyl)-4,5-dihydro-1H-benzofuro[2,3-d]azepine-3(2H)-carboxylateYield 62%

Procedure

The product of step D and sodium benzenesulfinate were coupled using the procedure of Example 29 step C. Purification by flash column chromatography (SiO2, 9:1 to 1:1 hexanes/ethyl acetate) afforded ethyl 7-chloro-9-(phenylsulfonyl)-4,5-dihydro-1H-benzofuro[2,3-d]azepine-3(2H)-carboxylate (35 mg, 62%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.00-7.92. (m, 3H), 7.80 (s, 1H), 7.62-7.48 (m, 3H), 4.20 (q, J=7.1 Hz, 2H), 3.80-3.68 (m, 4H), 3.22-3.11 (m, 2H), 2.96-2.82 (m, 2H), 1.29 (t, J=7.1 Hz, 3H).

Workup

  1. customPurification by flash column chromatography (SiO2, 9:1 to 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-c0998affa0ce48baa948a99080d653ab
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

Loading…