Sodium Carbonate → N-butyl-4-[2-(4-fluorophenyl)-7-(2-furyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine

HRID 1373842Notes

Reaction equation

HRID 1373842 reaction equation
[CH2:1]([NH:5][C:6]1[N:11]=[C:10]([C:12]2[C:13]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[N:14][N:15]3[C:20](Cl)=[CH:19][CH:18]=[CH:17][C:16]=23)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([NH:5][C:6]1[N:11]=[C:10]([C:12]2[C:13]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[N:14][N:15]3[C:20]([C:30]4[O:29][CH:33]=[CH:32][CH:31]=4)=[CH:19][CH:18]=[CH:17][C:16]=23)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 22174847N-butyl-4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine

Product 1

HCID 10137347N-butyl-4-[2-(4-fluorophenyl)-7-(2-furyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amineYield 39.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

A solution of N-butyl-4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]pyrimidin-2-amine (35 mg, 0.089 mmol), 2-furylboronic acid (30 mg, 0.27 mmol), sodium carbonate (155 μL, 2.0 M aqueous, 0.31 mmol), and dichlorobis(triphenylphosphine)palladium(II) (3 mg, 0.004 mmol) was heated at 90° C. for 4 hours. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (4:1 hexanes:ethyl acetate) provided N-butyl-4-[2-(4-fluorophenyl)-7-(2-furyl)pyrazolo[1,5-α]pyridin-3-yl]pyrimidin-2-amine (15 mg, 39%) as a yellow solid. Rf 0.19 (4:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 8.35 (d, 1H), 8.11–8.07 (m, 2H), 7.73 (m, 2H), 7.63 (s, 1H), 7.57 (d, 1H), 7.43 (t, 1H), 7.16 (t, 2H), 6.66 (m, 1H), 6.41 (d, 1H), 5.17 (m, 1H), 3.50 (q, 2H), 1.67 (m, 2H), 1.49 (m, 2H), 0.99 (t, 3H); MS m/z 428 (M+1).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-fd3b3ec626004adab7261c0b8e33c96c
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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