HCID 10205198, compound → HCID 10178283, compound

HRID 456710Notes

Reaction equation

HRID 456710 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:30])[C:5]2[N:6]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[N:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1>C(O)C.[Pd]>[CH:25]1([NH:24][C:20]2[N:19]=[C:18]([C:8]3[N:6]4[CH:7]=[CH:2][CH:3]=[C:4]([CH3:30])[C:5]4=[N:10][C:9]=3[C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[CH:23]=[CH:22][N:21]=2)[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

4

Reactant 1

HCID 10205198HCID 10205198, compound

Product 1

HCID 10178283HCID 10178283, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-{4-[6-Bromo-2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyridin-3-yl]-2-pyrimidinyl}-N-cyclopentylamine (120 mg, 0.26 mmol) was dissolved in ethanol. To this solution was added 10% palladium on charcoal and the reaction was stirred under hydrogen atmosphere (1 atm) at room temperature for 3 hours. The catalyst was removed by filtration and the resulting solution concentrated to a solid. This solid was purified by silica gel chromatography (1:1 ethyl acetate:hexane) to give 70 mg (70%) of N-cyclopentyl-4-[2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyridin-3-yl]-2-pyrimidinamine as a yellowish foam. 1H NMR (CDCl3) δ 9.45 (d, 1H), 8.12 (d, 1H), 7.67 (q, 2H), 7.15 (m, 3H), 6.86 (t, 1H), 6.39 (d, 1H), 5.26 (d, 1H), 4.41 (m, 1H), 2.71 (s, 3H), 2.0–2.1 (m, 2H), 1.4–1.9 (m, 6H); 19F NMR (CDCl3) δ −113.7;

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe resulting solution concentrated to a solid
  3. customThis solid was purified by silica gel chromatography (1:1 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-a5bed7950df34ec28c383ca74454a2a1
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

Loading…