Diethyl Ether → HCID 10109822, compound

HRID 1373806Notes

Reaction equation

HRID 1373806 reaction equation
Br[C:2]1[C:3]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[N:4][N:5]2[C:10]([NH:11][CH:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][C:6]=12.[N:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].CCOCC>CN(C)C=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>[CH:12]1([NH:11][C:10]2[N:5]3[N:4]=[C:3]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=4)[C:2]([C:27]4[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=4)=[C:6]3[CH:7]=[CH:8][CH:9]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 69447740HCID 69447740, compound

Product 1

HCID 10109822HCID 10109822, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-N-cyclopentyl-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (106 mg, 0.28 mmol) in N,N-dimethylformamide (5 mL) was added 4-pyridinylboronic acid (70 mg, 0.56 mmol), sodium carbonate (0.28 mL, 2 M aqueous, 0.56 mmol) and dichlorobis(triphenylphosphine)palladium(II) (10 mg, 0.01 mmol). The resultant solution was heated to 100° C. for 18 hours. The reaction mixture was cooled to room temperature and ether was added. The organic layer was washed with water and brine. The aqueous layer was extracted with ether and the combined organics dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 hexanes:ether) provided N-cyclopentyl-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridin-7-amine (48 mg, 46%) as a yellow solid. 1H NMR (CDCl3): δ 8.50 (d, 2H), 7.53 (m, 2H), 7.22–7.18 (m, 3H), 7.06–6.97 (m, 3H), 6.00 (d, 1H), 5.95 (d, 1H), 3.99 (m, 1H), 2.16–2.08 (m, 2H), 1.83–1.66 (m, 6H); 13C NMR (CDCl3) δ 162.99 (d, JCF=246.6 Hz), 150.07, 149.98, 142.77, 141.98, 140.13, 131.02 (d, JCF=8.0 Hz), 129.04, 127.64, 123.98, 115.56 (d, JCF=21.2 Hz), 106.51, 102.22, 89.25, 53.88, 33.36, 24.05; 19F NMR (CDCl3) δ −113.49; MS m/z 373 (M+1).

Workup

  1. washThe organic layer was washed with water and brine
  2. extractionThe aqueous layer was extracted with ether
  3. dry with materialthe combined organics dried over magnesium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-cc14ae176cae421f8b6dad3eb76d9e08
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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