HCID 131733908, compound → HCID 117760185, compound

HRID 709730Notes

Reaction equation

HRID 709730 reaction equation
[CH3:1][C:2]([CH3:34])([CH3:33])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10][O:11][C:12]2[N:17]=[C:16]([CH3:18])[N:15]=[C:14]([CH:19]=[CH:20][C:21]([OH:23])=[O:22])[CH:13]=2)[CH:7]=[CH:6][C:5]=1[C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[F:32]>C1COCC1.C(OCC)(=O)C.[Pd]>[CH3:1][C:2]([CH3:34])([CH3:33])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10][O:11][C:12]2[N:17]=[C:16]([CH3:18])[N:15]=[C:14]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:13]=2)[CH:7]=[CH:6][C:5]=1[C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[F:32]

Participants

5

Reactant 1

HCID 131733908HCID 131733908, compound

Product 1

HCID 117760185HCID 117760185, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(6-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-2-methylpyrimidin-4-yl)acrylic acid (330 mg) in THF (5.0 mL) and ethyl acetate (5.0 mL) was added 10% palladium-activated carbon (30 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 2 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (153 mg) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d2141064e4e6460ea4b301d6cd2cd315
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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