HCID 50998759, compound → HCID 68108368, compound

HRID 2179325Notes

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

Participants

Reactant 2

HCID 50998759HCID 50998759, compound

HCID 68109313HCID 68109313, compound

Product 1

HCID 68108368HCID 68108368, compoundYield 50%

Procedure

The product of Example 29, step B and sodium 3,5-difluorobenzenesulfinate 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-(3,5-difluorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (191 mg, 50%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.08 (s, 1H), 7.82 (dd, J=8.4, 1.8 Hz, 1H), 7.55 (d, J=8.7 Hz, 1H), 7.49-7.45 (m, 2H), 7.02-6.94 (m, 1H), 4.59 (s, 2H), 3.84 (t, J=5.4 Hz, 2H), 2.91-2.84 (m, 2H), 1.51 (s, 9H).

Workup

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

Sources & evidence

ORD record: ord-0fe97459e42644b1ace44f89edbdcf27
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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