(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 → (S)-7-Benzyloxy-2-(4-fluoro-phenyl)-9-methanesulfonyl-5-methyl-8,9-dihydro-7H-1-oxa-9,10-diaza-cyclohepta[f]indene-3-carboxylic acid methylamide

HRID 2190178Notes

Reaction equation

[CH2:1]([O:8][C@@H:9]([CH:39]=C)[CH2:10][N:11]([C:16]1[N:21]=[C:20]2[O:22][C:23]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[C:24]([C:25]([NH:27][CH3:28])=[O:26])[C:19]2=[CH:18][C:17]=1[C:36]([CH3:38])=C)[S:12]([CH3:15])(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[CH3:28][NH:27][C:25]([C:24]1[C:19]2[CH:18]=[C:17]3[C:36]([CH3:38])=[CH:39][C@H:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:10][N:11]([S:12]([CH3:15])(=[O:13])=[O:14])[C:16]3=[N:21][C:20]=2[O:22][C:23]=1[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)=[O:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (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 (543 mg, 0.963 mmol) in toluene is added Hoveyda-Grubbs 2nd generation catalyst (6 mg, 0.0096 mmol), and the reaction mixture is heated to 100° C. for 18 h. After the reaction is judged complete by LCMS, the toluene is removed in vacuo, and the solid is triturated with methanol to afford (S)-7-Benzyloxy-2-(4-fluoro-phenyl)-9-methanesulfonyl-5-methyl-8,9-dihydro-7H-1-oxa-9,10-diaza-cyclohepta[f]indene-3-carboxylic acid methylamide that is taken directly to the next step.

Workup

customthe toluene is removed in vacuo
customthe solid is triturated with methanol

Sources & evidence

ORD record: ord-58d8854e7fa14ed5ac8d5b161c4dc1b1
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324239B2

Reaction notes

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