Potassium vinyltrifluoroborate → 2-(4-Fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-vinylfuro[2,3-b]pyridine-3-carboxamide

HRID 2190179Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:24][C:11]3=[N:12][C:13]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:14]([C:16](C)=[CH2:17])[CH:15]=[C:10]3[C:9]=2[C:25]([NH:27][CH3:28])=[O:26])=[CH:4][CH:3]=1.C([B-](F)(F)F)=C.[K+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:24][C:11]3=[N:12][C:13]([NH:19][S:20]([CH3:23])(=[O:21])=[O:22])=[C:14]([CH:16]=[CH2:17])[CH:15]=[C:10]3[C:9]=2[C:25]([NH:27][CH3:28])=[O:26])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 23679353Potassium vinyltrifluoroborate

HCID 580523332-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide

Product 1

HCID 580524062-(4-Fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-vinylfuro[2,3-b]pyridine-3-carboxamide

Procedure

2-(4-Fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-vinylfuro[2,3-b]pyridine-3-carboxamide is prepared by analogy to 2-(4-Fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide, step A of Example 33. Potassium vinyltrifluoroborate may be used as the coupling partner.

Sources & evidence

ORD record: ord-0d4874ac7060420095e3de909d426679
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324239B2

Reaction notes

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