Diethyl Ether → HCID 86616860, compound

HRID 1373804Notes

Reaction equation

HRID 1373804 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[CH:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+].CCOCC>O1CCCC1>[Br:18][C:10]1[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:8][N:7]2[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=12

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 111841947-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine

Product 1

HCID 86616860HCID 86616860, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (0° C.) solution of 7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridine (5.0 g, 20.2 mmol) in tetrahydrofuran (81 mL) was added N-bromosuccinimide (3.79 g, 21.2 mmol) in two portions. The solution solidified after 5 minutes and additional tetrahydrofuran was added (20 mL). The resultant solution was stirred for 15 minutes. Saturated aqueous sodium bicarbonate and ether were added and the layers separated. The organic layer was washed with brine. The aqueous layers were extracted with ethyl acetate and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by recrystallization from ethyl acetate-hexane-methanol provided 3-bromo-7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridine (5.7 g, 87%) as a crystalline solid. 1H NMR (CDCl3) δ 8.07 (dd, 2H), 7.53 (d, 1H), 7.23–7.16 (m, 3H), 6.98 (d, 1H); 19F NMR (CDCl3) δ −112.60; MS m/z 325 (M+1).

Workup

  1. customthe layers separated
  2. washThe organic layer was washed with brine
  3. extractionThe aqueous layers were extracted with ethyl acetate
  4. dry with materialthe combined organics were dried over magnesium sulfate
  5. filtrationFiltration and concentration
  6. customfollowed by recrystallization from ethyl acetate-hexane-methanol

Sources & evidence

ORD record
ord-9c66dddb774848929e2aded09a7cca34
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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