Benzenesulfinic acid, sodium salt → HCID 68108892, compound

HRID 2179383Notes

Reaction equation

[N:1]1([CH2:6][C:7]2[C:12]3[O:13][C:14]4[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][C:15]=4[C:11]=3[CH:10]=[C:9](Br)[CH:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[C:28]1([S:34]([O-:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Na+]>>[N:1]1([CH2:6][C:7]2[C:12]3[O:13][C:14]4[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][C:15]=4[C:11]=3[CH:10]=[C:9]([S:34]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:36])=[O:35])[CH:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium salt

HCID 68109526HCID 68109526, compound

Product 1

HCID 68108892HCID 68108892, compoundYield 39%

Procedure

The product of step B and sodium benzenesulfinate were coupled using the procedure of Example 29, step C. Purification by flash chromatography (SiO2, 80:20 hexanes/ethyl acetate) provided tert-butyl 6-((1H-pyrazol-1-yl)methyl)-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (18 mg, 39%) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.05-7.96 (m, 1H), 7.95-7.85 (m, 2H), 7.62-7.40 (m, 6H), 6.32-6.25 (m, 1H), 5.60 (s, 2H), 4.56 (s, 2H), 3.83 (t, J=5.1 Hz, 2H), 2.95-2.80 (m, 2H), 1.51 (s, 9H).

Workup

customPurification by flash chromatography (SiO2, 80:20 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-b414ed86bef84e0ab243def7351c61ae
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

Loading…