Benzenesulfinic acid, sodium salt → tert-butyl 3-(acetoxymethyl)-6-chloro-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

HRID 2179415Notes

Reaction equation

[C:1]([O:4][CH2:5][CH:6]1[N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH:9]2[C:19]3[CH:25]=[C:24](Br)[CH:23]=[C:22]([Cl:27])[C:20]=3[O:21][CH:8]2[CH2:7]1)(=[O:3])[CH3:2].[C:28]1([S:34]([O-:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Na+]>>[C:1]([O:4][CH2:5][CH:6]1[N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][C:9]2[C:19]3[CH:25]=[C:24]([S:34]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:36])=[O:35])[CH:23]=[C:22]([Cl:27])[C:20]=3[O:21][C:8]=2[CH2:7]1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium salt

HCID 68108210tert-butyl 3-(acetoxymethyl)-8-bromo-6-chloro-1,4,4a,9b-tetrahydrobenzofuro[3,2-c]pyridine-2(3H)-carboxylate

Product 1

HCID 68109871tert-butyl 3-(acetoxymethyl)-6-chloro-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 84%

Procedure

The product from step J and sodium benzenesulfinate were coupled following the procedure of Example 29 step C. The crude product was purified by flash column chromatography (SiO2, 9:1 to 7:3, hexanes/ethyl acetate) to give tert-butyl 3-(acetoxymethyl)-6-chloro-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (110 mg, 84%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 7.98-7.95 (m, 3H), 7.86 (s, 1H), 7.58-7.49 (m, 3H), 5.10 (br s, 2H), 4.20-4.04 (m, 3H), 3.22-3.14 (m, 1H), 2.81 (d, J=17.4 Hz, 1H), 2.04 (s, 3H), 1.53 (s, 9H).

Workup

customThe crude product was purified by flash column chromatography (SiO2, 9:1 to 7:3, hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-b4309a0db5ff427eb0b01cd3fabd4cd3
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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