Sodium 3-chlorobenzene-1-sulfinate → tert-butyl 8-(3-chlorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

HRID 2179313Notes

Reaction equation

HRID 2179313 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:14][C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=3[C:6]=2[CH:7]=1.[Cl:22][C:23]1[CH:24]=[C:25]([S:29]([O-:31])=[O:30])[CH:26]=[CH:27][CH:28]=1.[Na+]>>[Cl:22][C:23]1[CH:24]=[C:25]([S:29]([C:2]2[CH:3]=[CH:4][C:5]3[O:14][C:13]4[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=4[C:6]=3[CH:7]=2)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 23677431Sodium 3-chlorobenzene-1-sulfinateHCID 68109313HCID 68109313, compound

Product 1

HCID 68109082tert-butyl 8-(3-chlorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 26.8%

Procedure

The product of Example 29, step B (230 mg, 0.65 mmol) and sodium 3-chlorobenzenesulfinate (155 mg, 0.78 mmol) were coupled using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 3:2 hexanes/ethyl acetate) provided tert-butyl 8-(3-chlorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (78 mg, 26%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.08 (s, 1H), 7.93 (t, J=1.8 Hz, 1H), 7.86-7.83 (m, 1H), 7.83-7.81 (m, 1H), 7.56-7.48 (m, 2H), 7.43 (t, J=7.8 Hz, 1H), 4.58 (s, 2H), 3.84 (t, J=5.4 Hz, 2H), 2.91-2.84 (m, 2H), 1.51 (s, 9H).

Workup

  1. customPurification by flash column chromatography (SiO2, 3:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-acfd1f8123ee4440bc88aa32bcb51a4a
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

Loading…