Sodium 3-(trifluoromethyl)benzene-1-sulfinate → tert-butyl 6-chloro-8-(3-trifluoromethylphenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

HRID 2179338Notes

Reaction equation

HRID 2179338 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:10]=3[C:6]=2[CH:5]=[C:4](Br)[CH:3]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([S:31]([O-:33])=[O:32])[CH:28]=[CH:29][CH:30]=1.[Na+]>>[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:10]=3[C:6]=2[CH:5]=[C:4]([S:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([F:23])([F:34])[F:35])[CH:26]=2)(=[O:33])=[O:32])[CH:3]=1

Participants

3

Reactant 2

HCID 23677070Sodium 3-(trifluoromethyl)benzene-1-sulfinateHCID 68109024tert-butyl 6-chloro-8-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Product 1

HCID 68109217tert-butyl 6-chloro-8-(3-trifluoromethylphenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 33%

Procedure

The product of Example 44, step B was coupled with sodium 3-trifluoromethylbenzenesulfinate using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 3:2 hexane/ethyl acetate) provided tert-butyl 6-chloro-8-(3-trifluoromethylphenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (130 mg, 33%) as an off-white solid: 1H NMR (CDCl3, 400 MHz) δ 8.26 (s, 1H), 8.15 (d, J=8.0 Hz, 1H), 7.94-8.06 (m, 1H), 7.86-7.81 (m, 2H), 7.73-7.63 (m, 1H), 4.58 (m, 2H), 3.84 (m, 2H), 2.92 (m, 2H), 1.48 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-d9535ef66fcf4cd2951016fd2e6dd9a1
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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