HCID 90333624, compound → HCID 90333458, compound

HRID 595770Notes

Reaction equation

HRID 595770 reaction equation
C([O:8][CH2:9][CH:10]([C:12]1[CH:13]=[CH:14][C:15]([C:28]2[C:29]([N:48]([CH3:53])[S:49]([CH3:52])(=[O:51])=[O:50])=[CH:30][C:31]3[O:35][C:34]([C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)=[C:33]([C:43]([NH:45][CH3:46])=[O:44])[C:32]=3[CH:47]=2)=[N:16][C:17]=1[C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[C:24]([F:27])[CH:23]=[CH:22][CH:21]=2)[F:11])C1C=CC=CC=1>C1COCC1.[OH-].[Pd+2].[OH-]>[F:27][C:24]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:25]=1[CH:26]=[C:18]([C:17]1[N:16]=[C:15]([C:28]3[C:29]([N:48]([CH3:53])[S:49]([CH3:52])(=[O:51])=[O:50])=[CH:30][C:31]4[O:35][C:34]([C:36]5[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=5)=[C:33]([C:43]([NH:45][CH3:46])=[O:44])[C:32]=4[CH:47]=3)[CH:14]=[CH:13][C:12]=1[CH:10]([F:11])[CH2:9][OH:8])[NH:19]2

Participants

4

Reactant 1

HCID 90333624HCID 90333624, compound

Product 1

HCID 90333458HCID 90333458, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(5-(2-(benzyloxy)-1-fluoroethyl)-6-(4-fluoro-1H-indol-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (530 mg, 0.717 mmol) in THF (10 mL) was added palladium hydroxide (101 mg, 0.717 mmol). The mixture was hydrogenated under a balloon for 2 h. Filtration through a pad of celite removed the solid. After washing with ethyl acetate, the combined filtrate was concentrated in vacuo to give 5-(6-(4-fluoro-1H-indol-2-yl)-5-(1-fluoro-2-hydroxyethyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (465 mg, yield: 100%). MS (M+H)+: 649.

Workup

  1. filtrationFiltration through a pad of celite
  2. customremoved the solid
  3. washAfter washing with ethyl acetate
  4. concentrationthe combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bae28d17a5fb49aab0f8b9435ce026aa
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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