Sodium 4-methoxybenzene-1-sulfinate → tert-butyl 8-(4-methoxyphenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

HRID 2179319Notes

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.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O-:32])=[O:31])=[CH:26][CH:25]=1.[Na+]>>[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([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:32])=[O:31])=[CH:28][CH:29]=1

Participants

Reactant 2

HCID 23680956Sodium 4-methoxybenzene-1-sulfinate

HCID 68109313HCID 68109313, compound

Product 1

HCID 68109112tert-butyl 8-(4-methoxyphenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 41%

Procedure

The product of Example 29, step B and sodium 4-methoxybenzenesulfinate were coupled using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 4:1 hexane/ethyl acetate) provided tert-butyl 8-(4-methoxyphenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (221 mg, 41%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.05 (s, 1H), 7.90-7.86 (m, 2H), 7.79 (d, J=9.0 Hz, 1H), 7.48 (d, J=8.7 Hz, 1H), 6.98-6.91 (m, 2H), 4.56 (s, 2H), 3.83 (m, 5H), 2.86 (m, 2H), 1.50 (s, 9H).

Workup

customPurification by flash column chromatography (SiO2, 4:1 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-21a1383f8c224ead9b756af81e40d053
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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