Benzenesulfinic acid, sodium salt → HCID 68109925, compound

HRID 2179345Notes

Reaction equation

[F: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.[C:23]1([S:29]([O-:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Na+]>>[F: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:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])[CH:3]=1

Participants

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium salt

HCID 68109270HCID 68109270, compound

Product 1

HCID 68109925HCID 68109925, compoundYield 57%

Procedure

The product of step B was coupled with sodium benzenesulfinate using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 7:3 hexane/ethyl acetate) provided tert-butyl 6-fluoro-8-phenylsulfonyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (141 mg, 57%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.97-7.94 (m, 2H), 7.88 (br s, 1H), 7.61-7.47 (m, 4H), 4.57 (s, 2H), 3.84 (t, J=5.4 Hz, 2H), 2.89 (br s, 2H), 1.51 (s, 9H).

Workup

customPurification by flash column chromatography (SiO2, 7:3 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-2f17d652f86a443b8a275402c68a72bf
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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