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

HRID 2179321Notes

Reaction equation

HRID 2179321 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]([C:24]1[CH:29]=[CH:28][C:27]([S:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)#[N:23].[Na+]>>[C:22]([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)#[N:23]

Participants

3

Reactant 2

HCID 23668300Sodium 4-cyanobenzenesulfinateHCID 68109313HCID 68109313, compound

Product 1

HCID 68109181tert-butyl 8-(4-cyanophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 34%

Procedure

The product of Example 29, step B and sodium 4-cyanobenzenesulfinate 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-cyanophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (107 mg, 34%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.09-8.03 (m, 3H), 7.84 (dd, J=5.7, 3.9 Hz, 1H), 7.80-7.76 (m, 2H), 7.55 (d, J=8.4 Hz, 1H), 4.58 (s, 2H), 3.84 (t, J=5.7 Hz, 2H), 2.91-2.82 (m, 2H), 1.51 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-25655beca68f4433b927301256633cff
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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