Sodium 3-chlorobenzene-1-sulfinate → tert-butyl 7-(3-chlorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

HRID 2179355Notes

Reaction equation

HRID 2179355 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[CH2:9][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:12][C:13]=3[O:14][C:4]=2[CH:3]=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:7]=[CH:6][C:5]3[C:8]4[CH2:9][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:12][C:13]=4[O:14][C:4]=3[CH:3]=2)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 23677431Sodium 3-chlorobenzene-1-sulfinateHCID 68109423tert-butyl 7-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Product 1

HCID 68109098tert-butyl 7-(3-chlorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 52%

Procedure

The product of step A was coupled with sodium 3-chlorobenzenesulfinate following the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 100:0 to 30:70 hexanes/ethyl acetate) provided tert-butyl 7-(3-chlorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (66 mg, 52%) as an oil: 1H NMR (CDCl3, 300 MHz) δ 8.06 (d, J=1.3 Hz, 1H), 7.92 (t, J=1.9 Hz, 1H), 7.83 (td, J=7.9, 1.4 Hz, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.53 (d, J=8.2 Hz, 1H), 7.50 (m, 1H), 7.42 (t, J=7.9 Hz, 1H), 4.55 (br s, 2H), 3.83 (br s, 2H), 2.89 (br s, 2H), 1.49 (s, 9H).

Workup

  1. customPurification by flash column chromatography (SiO2, 100:0 to 30:70 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-06866aa84c0141bb8ab1dc85e8c17ecf
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

Loading…