HCID 23675619, compound → HCID 68109050, compound

HRID 2179330Notes

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

Participants

Reactant 2

HCID 23675619HCID 23675619, compound

HCID 68109313HCID 68109313, compound

Product 1

HCID 68109050HCID 68109050, compoundYield 85%

Procedure

The product of Example 29, step B and sodium 2-naphthylsulfinate were coupled using the procedure of Example 29, step C. Purification by flash column chromatography (SiO2, 80:20 hexane/ethyl acetate) provided tert-butyl 8-(2-naphthylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (450 mg, 85%) as an orange solid: 1H NMR (CDCl3, 300 MHz) δ 8.58 (s, 1H), 8.14 (s, 1H), 8.02-7.82 (m, 5H), 7.66-7.56 (m, 2H), 7.50 (d, J=8.7 Hz, 1H), 4.57 (s, 2H), 3.82 (t, J=5.4 Hz, 2H), 2.90-2.80 (m, 2H), 1.50 (s, 9H).

Workup

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

Sources & evidence

ORD record: ord-5ac6e02ed6494feeb29a08345b869a2c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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