Benzenesulfinic acid, sodium salt → HCID 68108935, compound

HRID 2179379Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:22][OH:23])[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:24]1([S:30]([O-:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Na+]>>[OH:23][CH2:22][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:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])[CH:3]=1

Participants

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium salt

HCID 68109355HCID 68109355, compound

Product 1

HCID 68108935HCID 68108935, compoundYield 44%

Procedure

The product of step E and sodium benzenesulfinate were coupled using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 1:1 hexane/ethyl acetate) provided tert-butyl 6-(hydroxymethyl)-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (33 mg, 44%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 8.03 (s, 1H), 7.99-7.93 (m, 2H), 7.88 (d, J=1.6 Hz, 1H), 7.58-7.46 (m, 3H), 4.99 (d, J=6.0 Hz, 2H), 4.56 (s, 2H), 3.82 (s, 2H), 2.87 (s, 2H), 2.13 (t, J=6.0 Hz, 1H), 1.51 (s, 9H).

Workup

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

Sources & evidence

ORD record: ord-03fda69531c94b119d161e74e08cc453
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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