Sodium p-toluenesulfinate → HCID 68109342, compound

HRID 2179322Notes

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][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.[Na+]>>[CH3:22][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 2723791Sodium p-toluenesulfinate

HCID 68109313HCID 68109313, compound

Product 1

HCID 68109342HCID 68109342, compoundYield 33%

Procedure

The product of Example 29, step B and sodium 4-methylbenzenesulfinate were coupled using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 90:10 to 50:50 hexane/ethyl acetate) provided tert-butyl 8-(4-methylphenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (65 mg, 33%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 8.07 (br s, 1H), 7.86-7.78 (m, 3H), 7.49 (d, J=8.7 Hz, 1H), 7.28 (d, J=8.1 Hz, 2H), 4.57 (br s, 2H), 3.88-3.78 (m, 2H), 2.90-2.82 (m, 2H), 2.38 (s, 3H), 1.51 (s, 9H).

Workup

customPurification by flash column chromatography (SiO2, 90:10 to 50:50 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-e0a08e3c1069431e88078e2199f8a51a
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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