Cesium carbonate → (S)-6-(N-(2-(benzyloxy)but-3-enyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide

HRID 2190177Notes

Reaction equation

HRID 2190177 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]([CH3:18])=[CH2:17])[CH:15]=[C:10]3[C:9]=2[C:25]([NH:27][CH3:28])=[O:26])=[CH:4][CH:3]=1.I[CH2:30][C@@H:31]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:32]=[CH2:33].C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:35]([O:34][C@@H:31]([CH:32]=[CH2:33])[CH2:30][N:19]([C:13]1[N:12]=[C:11]2[O:24][C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[C:9]([C:25]([NH:27][CH3:28])=[O:26])[C:10]2=[CH:15][C:14]=1[C:16]([CH3:18])=[CH2:17])[S:20]([CH3:23])(=[O:21])=[O:22])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 22831641(S)-((1-iodobut-3-en-2-yloxy)methyl)benzeneHCID 580523332-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide

Product 1

HCID 54575747(S)-6-(N-(2-(benzyloxy)but-3-enyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamideYield 57.6%

Procedure

2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide (87 mg, 0.216 mmol), (S)-((1-iodobut-3-en-2-yloxy)methyl)benzene (62.1 mg, 0.216 mmol) and cesium carbonate (70.3 mg, 0.216 mmol) are heated under microwave irradiation for 30 min at 120° C. HPLC affords (S)-6-(N-(2-(benzyloxy)but-3-enyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide (70 mg, 0.124 mmol, 57.6% yield)

Sources & evidence

ORD record
ord-aca66e41c6ab4014ab9226fb0914b807
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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