HCID 178525086, compound → HCID 178525797, compound

HRID 2274780Notes

Reaction equation

HRID 2274780 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][N:23]([C@H:25]4[CH2:28][C@H:27]([C:29]([O:31]CC5C=CC=CC=5)=[O:30])[CH2:26]4)[CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][N:23]([C@H:25]4[CH2:28][C@H:27]([C:29]([OH:31])=[O:30])[CH2:26]4)[CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178525086HCID 178525086, compound2×

Product 1

HCID 178525797HCID 178525797, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of trans-benzyl 3-(4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)cyclobutanecarboxylate (Intermediate 34A; 500 mg; 0.944 mmol) and Pd/C (50 mg) in MeOH (50 mL) was stirred overnight under a hydrogen balloon. The reaction mixture was filtered and the filtrate was concentrated and purified by reverse phase flash chromatography to afford 113 mg (27%) of the title compound as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified by reverse phase flash chromatography

Sources & evidence

ORD record
ord-70bfcdb1aee44a96aaa145f76eac7682
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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