HCID 58886641, compound → HCID 58886648, compound

HRID 1766803Notes

Reaction equation

HRID 1766803 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]=[CH2:23])=[CH:18][C:17]=2[F:24])=[C:7]([F:14])[C:8]2[N:9]([CH:11]=[CH:12][N:13]=2)[CH:10]=1)=[O:4]>C(O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:6]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:17]=2[F:24])=[C:7]([F:14])[C:8]2[N:9]([CH:11]=[CH:12][N:13]=2)[CH:10]=1)=[O:4]

Participants

4

Reactant 1

HCID 58886641HCID 58886641, compound

Product 1

HCID 58886648HCID 58886648, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8-Fluoro-7-(2-fluoro-4-vinyl-phenylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (165 mg, 0.50 mmol) was suspended in ethanol (5 mL), added 10% Pd/C (267 mg, 0.25 mmol) and placed under an atmosphere of H2. The reaction mixture was stirred vigorously at room temperature for 16 hours. The reaction mixture was filtered through celite, washed with ethanol and tetrahydrofuran and the filtrate concentrated to a yellow oil. Purification of the crude product by flash column chromatography (gradient of dichloromethane to 20:1 dichloromethane/methanol) provided the desired product (110 mg, 66%) as a dark yellow solid. MS ESI (+) in/z 332 (M+1) detected.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with ethanol and tetrahydrofuran
  3. concentrationthe filtrate concentrated to a yellow oil
  4. customPurification of the crude product by flash column chromatography (gradient of dichloromethane to 20:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-1ac5c735bf7641cea235ad74be70a89f
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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