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

HRID 2179328Notes

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.[C:22]1([S:32]([O-:34])=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.[Na+]>>[C:22]1([S:32]([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:34])=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1

Participants

Reactant 2

HCID 23681220Sodium naphthalene-1-sulfinate

HCID 68109313HCID 68109313, compound

Product 1

HCID 68108679tert-butyl 8-(1-naphthylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 26%

Procedure

The product of Example 29, step B and sodium 1-naphthylsulfinate 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-(1-naphthylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (76 mg, 26%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 8.67 (d, J=8.1 Hz, 1H), 8.51 (dd, J=7.5, 1.2 Hz, 1H), 8.18-8.01 (m, 2H), 7.92-7.76 (m, 2H), 7.67-7.41 (m, 4H), 4.58-4.47 (m, 2H), 3.81 (br s, 2H), 2.83 (br s, 2H), 1.50 (s, 9H).

Workup

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

Sources & evidence

ORD record: ord-123626ca9e8345b389640b930efccb0f
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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