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

HRID 2179373Notes

Reaction equation

HRID 2179373 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]1[CH:25]=[C:26]([S:30]([O-:32])=[O:31])[CH:27]=[CH:28][CH:29]=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:30]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([F:23])[CH:25]=2)(=[O:32])=[O:31])[CH:3]=1

Participants

3

Reactant 2

HCID 23717246Sodium 3-fluorobenzene-1-sulfinateHCID 68109024tert-butyl 6-chloro-8-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Product 1

HCID 68108420tert-butyl 6-chloro-8-(3-fluorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 37%

Procedure

The product of Example 44, step B and sodium 3-fluorobenzenesulfinate were coupled using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 80:20 hexane/ethyl acetate) provided tert-butyl 6-chloro-8-((3-fluorophenyl)sulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (172 mg, 37%) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.01-7.91 (m, 1H), 7.83 (s, 1H), 7.80-7.73 (m, 1H), 7.70-7.62 (m, 1H), 7.60-7.45 (m, 2H), 4.57 (s, 2H), 3.84 (s, 2H), 2.91 (s, 2H), 1.51 (s, 9H).

Workup

  1. customPurification by flash column chromatography (SiO2, 80:20 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-daeb5e019e14405e83020b7d8a4491c4
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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