Cyclopentylamine → HCID 69447740, compound

HRID 1373805Notes

Reaction equation

HRID 1373805 reaction equation
[Br:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:4][N:5]2[C:10](Cl)=[CH:9][CH:8]=[CH:7][C:6]=12.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:25]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26]1.CCOCC>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:4][N:5]2[C:10]([NH:30][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:9][CH:8]=[CH:7][C:6]=12

Participants

8

Reactant 4

HCID 2906CyclopentylamineHCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 86616860HCID 86616860, compound

Product 1

HCID 69447740HCID 69447740, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Procedure

To a solution of 3-bromo-7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridine (1.26 g, 3.9 mmol) in toluene (39 mL) was added successively racemic-BINAP (153 mg, 0.23 mmol), cesium carbonate (1.44 g, 3.9 mmol), cyclopentylamine (1.14 mL, 11.5 mmol), and palladium (II) acetate (35 mg, 0.15 mmol). The resultant mixture was heated at 95° C. for 2.5 hours at which time the reaction was judged complete by thin layer chromatography. The solution 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 (100:1 to 40:1 hexanes:ether) provided 3-bromo-N-cyclopentyl-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (1.2 g, 83%) as a white crystalline solid upon standing. 1H NMR (CDCl3): δ 8.05 (dd, 2H), 7.22–7.14 (m, 3H), 6.87 (d, 1H), 5.95–5.92 (m, 2H), 4.00 (m, 1H). 2.13 (m, 2H), 1.84–1.67 (m, 6H); 19F NMR (CDCl3) δ −113.44; MS m/z 374 (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-1085a181c4ba42f8a5771b6598293385
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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