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

HRID 2179341Notes

Reaction equation

HRID 2179341 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([O-:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].[Na+].[Cl:13][C:14]1[C:19]2[O:20][C:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][C:22]=3[C:18]=2[CH:17]=[C:16](Br)[CH:15]=1>>[Cl:13][C:14]1[C:19]2[O:20][C:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][C:22]=3[C:18]=2[CH:17]=[C:16]([S:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)(=[O:11])=[O:10])[CH:15]=1

Participants

3

Reactant 2

HCID 58258873Sodium 3-cyanobenzenesulfinateHCID 68109024tert-butyl 6-chloro-8-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Product 1

HCID 68109237tert-butyl 6-chloro-8-(3-cyanophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 12%

Procedure

Sodium 3-cyanobenzenesulfinate 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-(3-cyanophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (30 mg, 12%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 8.22-8.17 (m, 2H), 7.98 (s, 1H), 7.86-7.83 (m, 2H), 7.70-7.64 (m, 1H), 4.59 (s, 2H), 3.85 (t, J=5.7 Hz, 2H), 2.92 (t, J=5.7 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-636ea36b606e434e91c78444b6150bca
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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