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

HRID 2179340Notes

Reaction equation

HRID 2179340 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=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:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)(=[O:10])=[O:9])[CH:14]=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 41%

Procedure

Sodium 3-fluorobenzenesulfinate 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-fluorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (100 mg, 41%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 7.97 (s, 1H), 7.84-7.83 (d, J=1.5 Hz, 1H), 7.78-7.33 (m, 1H), 7.67-7.63 (m, 1H), 7.56-7.47 (m, 1H), 7.30-7.24 (m, 1H), 4.57 (s, 2H), 3.84 (t, J=5.4 Hz, 2H), 2.91 (t, J=5.4 Hz, 2H), 1.50 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-98d7912b08724ca19ac4a8cb792039ef
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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