Benzenesulfinic acid, sodium salt → tert-butyl 7-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

HRID 2179352Notes

Reaction equation

HRID 2179352 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[CH2:9][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:12][C:13]=3[O:14][C:4]=2[CH:3]=1.[C:22]1([S:28]([O-:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Na+]>>[C:22]1([S:28]([C:2]2[CH:7]=[CH:6][C:5]3[C:8]4[CH2:9][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:12][C:13]=4[O:14][C:4]=3[CH:3]=2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium saltHCID 68109423tert-butyl 7-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Product 1

HCID 68109015tert-butyl 7-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 29%

Procedure

The product of step C was coupled with sodium benzenesulfinate following the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 85:15 hexanes/ethyl acetate) provided tert-butyl 7-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (31 mg, 29%) as light yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.06 (d, J=1.2 Hz, 1H), 7.98-7.91 (m, 2H), 7.81 (dd, J=8.1 Hz, 1.2 Hz, 1H), 7.56-7.45 (m, 4H), 4.54 (s, 2H), 3.82 (t, J=5.4 Hz, 2H), 2.88 (t, J=5.7 Hz, 2H), 1.49 (s, 9H).

Workup

  1. customPurification by flash column chromatography (SiO2, 85:15 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-90f7fdc4eef44845bb416b14c3b08cfd
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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