HCID 131733910, compound → HCID 117759868, compound

HRID 709733Notes

Reaction equation

HRID 709733 reaction equation
[CH3:1][C:2]([CH3:35])([CH3:34])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10][O:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([CH:20]=[CH:21][C:22]([OH:24])=[O:23])[CH:13]=2)[CH:7]=[CH:6][C:5]=1[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=1[F:33]>C1COCC1.C(OCC)(=O)C.[Pd]>[CH3:1][C:2]([CH3:35])([CH3:34])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10][O:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:13]=2)[CH:7]=[CH:6][C:5]=1[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=1[F:33]

Participants

5

Reactant 1

HCID 131733910HCID 131733910, compound

Product 1

HCID 117759868HCID 117759868, compoundYield 25.4%

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-methoxypyrimidin-4-yl)acrylic acid (530 mg) in THF (5.0 ml) and ethyl acetate (5.0 mL) was added 10% palladium-activated carbon (53 mg) and, under a hydrogen atmosphere, the mixture was stirred 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 (135 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-149ccb2f4854404abe6570f7292a7a32
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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