Carbon Tetrachloride → HCID 10334377, compound

HRID 859966Notes

Reaction equation

HRID 859966 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([CH2:17][CH2:18][CH3:19])=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.C([Li])CCC.C(Cl)(Cl)(Cl)[Cl:26]>O1CCCC1>[Cl:26][C:16]1[N:11]2[N:10]=[C:9]([CH2:17][CH2:18][CH3:19])[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=3)=[C:12]2[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 100609173-(2-fluoropyridin-4-yl)-2-propylpyrazolo[1,5-a]pyridineHCID 178418339Butyllithium

Product 1

HCID 10334377HCID 10334377, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3-(2-fluoropyridin-4-yl)-2-propylpyrazolo[1,5-a]pyridine (109 mg, 0.42 mmol) in tetrahydrofuran (5 mL) was cooled to −78° C. Butyllithium (0.4 mL, 1.6 M in hexane, 0.64 mmol) was added dropwise and the resultant solution was stirred at −78° C. for 45 minutes. Carbon tetrachloride (0.3 mL) was added and the mixture was stirred at −78° C. for 30 minutes and then quenched byt the addition of methanol while cold. Upon warming to room temperature water and ether were added and the layers separated. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed flash chromatography on silica gel (4:1 to 2:1 hexane-ethyl acetate) provided 7-chloro-3-(2-fluoropyridin-4-yl)-2-propylpyrazolo[1,5-a]pyridine (77 mg, 63%) as an orange solid. 1H NMR (CDCl3) δ 8.33 (d, 1H), 7.58 (d, 1H), 7.30 (m, 1H), 7.22 (t, 1H), 7.02–6.98 (m, 2H), 2.99 (t (m, 2H), 1.01 (t, 3H); 19F NMR (CDCl3) δ −68.11; MS m/z 290 (M+1).

Workup

  1. customquenched byt the addition of methanol while cold
  2. temperatureUpon warming to room temperature water and ether
  3. additionwere added
  4. customthe layers separated
  5. washThe organic layer was washed with brine
  6. extractionThe aqueous layer was extracted with ether
  7. dry with materialthe combined organics were dried over magnesium sulfate
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-adeeabf077634771bd5805f1ba56f706
Source dataset
uspto-grants-2006_12
Patent number
US07153863B2

Reaction notes

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