Sodium 4-chlorobenzenesulfinate → tert-butyl 6-chloro-8-(4-chlorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

HRID 2179342Notes

Reaction equation

HRID 2179342 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Na+].[Cl:12][C:13]1[C:18]2[O:19][C:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][C:21]=3[C:17]=2[CH:16]=[C:15](Br)[CH:14]=1>>[Cl:12][C:13]1[C:18]2[O:19][C:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][C:21]=3[C:17]=2[CH:16]=[C:15]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:14]=1

Participants

3

Reactant 2

HCID 23664783Sodium 4-chlorobenzenesulfinateHCID 68109024tert-butyl 6-chloro-8-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Product 1

HCID 68108834tert-butyl 6-chloro-8-(4-chlorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 48%

Procedure

Sodium 4-chlorobenzenesulfinate was coupled with the product of Example 44, step B following the procedure of Example 29, step C. The crude product was purified by flash column chromatography (SiO2, 3:2 hexanes/ethyl acetate) to give tert-butyl 6-chloro-8-(4-chlorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (120 mg, 48%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 7.95 (s, 1H), 7.90-7.89 (m, 1H), 7.88-7.87 (m, 1H), 7.82-7.81 (m, 1H), 7.51-7.50 (m, 1H), 7.48-7.47 (m, 1H), 4.56 (s, 2H), 3.84 (t, J=5.4 Hz, 2H), 2.91 (t, J=5.4 Hz, 2H), 1.48 (s, 9H).

Workup

  1. customThe crude product was purified by flash column chromatography (SiO2, 3:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-9c961dc694a944dfba33be5c1ba07867
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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