4-fluorobenzenesulfinic acid sodium salt → HCID 68108445, compound

HRID 2179314Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[O:14][C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=3[C:6]=2[CH:7]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.[Na+]>>[F:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([C:2]2[CH:3]=[CH:4][C:5]3[O:14][C:13]4[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=4[C:6]=3[CH:7]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

Reactant 2

HCID 236662204-fluorobenzenesulfinic acid sodium salt

HCID 68109313HCID 68109313, compound

Product 1

HCID 68108445HCID 68108445, compoundYield 36%

Procedure

The product of Example 29, step B and sodium 4-fluorobenzenesulfinate were coupled using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 75:25 hexane/ethyl acetate) provided tert-butyl 8-(4-fluorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (217 mg, 36%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.07 (s, 1H), 8.01-7.91 (m, 2H), 7.81 (dd, J=8.7, 1.8 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.22-7.11 (m, 2H), 4.57 (s, 2H), 3.89-3.76 (m, 2H), 2.92-2.80 (m, 2H), 1.51 (s, 9H).

Workup

customPurification by flash column chromatography (SiO2, 75:25 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-33aa983fcb7446ea8b0d64a2b0ba20c7
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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