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

HRID 2179323Notes

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

Participants

Reactant 2

HCID 12249756Sodium 4-nitrobenzene-1-sulfinate

HCID 68109313HCID 68109313, compound

Product 1

HCID 68109579tert-butyl 8-(4-nitrophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 25%

Procedure

The product of Example 29, step B and sodium 4-nitrobenzenesulfinate were coupled using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 3:2 hexane/ethyl acetate) provided tert-butyl 8-(4-nitrophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (96 mg, 25%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.08 (s, 1H), 7.83 (dd, J=8.7, 1.8 Hz, 1H), 7.77-7.72 (m, 1H), 7.65 (dt, J=7.8, 2.1 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.50-7.44 (m, 1H), 7.25-7.20 (m, 1H), 4.58 (s, 2H), 3.84 (t, J=5.7 Hz, 2H), 2.91-2.82 (m, 2H), 1.55 (s, 9H).

Workup

customPurification by flash column chromatography (SiO2, 3:2 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-88a9bea4b94d4b6aa51b7c8eac71766a
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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