HCID 68109162, compound → HCID 68108961, compound

HRID 2179372Notes

Reaction equation

I[C:2]1[CH:15]=[CH:14][C:5]([CH2:6][O:7]C2CCCCO2)=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26]2[O:29][C:30]3[C:35]([Cl:36])=[CH:34][C:33]([S:37]([O-:39])=[O:38])=[CH:32][C:31]=3[C:25]=2[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].[Li+]>>[Cl:36][C:35]1[C:30]2[O:29][C:26]3[CH2:27][CH2:28][N:23]([C:21]([O:20][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:22])[CH2:24][C:25]=3[C:31]=2[CH:32]=[C:33]([S:37]([C:2]2[CH:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:14][CH:15]=2)(=[O:39])=[O:38])[CH:34]=1

Participants

Reactant 2

HCID 68109162HCID 68109162, compound

HCID 68109235HCID 68109235, compound

Product 1

HCID 68108961HCID 68108961, compoundYield 7%

Procedure

The product of step A was coupled with lithium 2-(tert-butoxycarbonyl)-6-chloro-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine-8-sulfinate following the procedure of Example 50, step A. The crude product was purified by flash column chromatography (SiO2, 7:3 hexanes/ethyl acetate) to give tert-butyl 6-chloro-8-((4-(hydroxymethyl)phenyl)sulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (30 mg, 7%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 8.02-7.89 (m, 3H), 7.82 (s, 1H), 7.53 (d, J=8.1 Hz, 2H), 4.77 (d, J=5.4 Hz, 2H), 4.56 (s, 2H), 3.83 (t, J=5.7 Hz, 2H), 2.97-2.85 (m, 2H) 1.50 (s, 9H).

Workup

customThe crude product was purified by flash column chromatography (SiO2, 7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-54d47f2c5f1140f7b6a5bf6bc869ee93
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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