Benzenesulfinic acid, sodium salt → HCID 68109753, compound

HRID 2179387Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:22](=[O:25])[NH:23][CH3:24])[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:26]1([S:32]([O-:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Na+]>>[CH3:24][NH:23][C:22]([C:4]1[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]=[C:2]([S:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:34])=[O:33])[CH:3]=1)=[O:25]

Participants

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium salt

HCID 68108989HCID 68108989, compound

Product 1

HCID 68109753HCID 68109753, compoundYield 68%

Procedure

The product of step A and sodium benzenesulfinate were coupled using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 1:4 dichloromethane/ethyl acetate) provided tert-butyl 6-(methylcarbamoyl)-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (41 mg, 68%) as a yellow oil: 1H NMR (CDCl3, 400 MHz) δ 8.54 (d, J=2.0 Hz, 1H), 8.18 (s, 1H), 7.97 (d, J=7.2 Hz, 2H), 7.59-7.44 (m, 3H), 7.28 (s, 1H), 4.59 (s, 2H), 3.87 (t, J=5.2 Hz, 2H), 3.10 (d, J=4.8 Hz, 3H), 3.00-2.88 (m, 2H), 1.51 (s, 9H).

Workup

customPurification by flash column chromatography (SiO2, 1:4 dichloromethane/ethyl acetate)

Sources & evidence

ORD record: ord-03aafa9f537c4d0a8436ee90045edfbe
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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