Water → HCID 18446594, compound

HRID 1269072Notes

Reaction equation

HRID 1269072 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)[C:10]([CH:11]=[O:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1.[C:18]([Mg]Br)#[CH:19].O>O1CCCC1>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)[C:10]([CH:11]([OH:12])[C:18]#[CH:19])=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18446628HCID 18446628, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 18446594HCID 18446594, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-chloro-2-(2-furyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (3.36 g, 13.6 mmol) in tetrahydrofuran (100 mL) at −78° C. was added ethynylmagnesium bromide (32.7 mL, 0.5 M in tetrahydrofuran, 16.3 mmol). The mixture was allowed to warm to room temperature and stirred for 1 hour. Water was added to the reaction and the resulting mixture was extracted with ethyl acetate. The ethyl acetate phase was dried over magnesium sulfate, filtered and concentrated to a solid residue, 1-[(7-chloro-2-(2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-ol (3.63 g, 98%). 1H NMR (CDCl3): δ 7.98 (d, 1H), 7.59 (d, 1H), 7.16 (t, 1H), 7.03 (d, 1H), 6.95 (d, 1H), 6.55 (m, 1H), 6.16 (m, 1H), 2.76 (m, 1H), 2.63 (s, 1H). MS m/z 273 (M+1).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a solid residue, 1-[(7-chloro-2-(2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-ol (3.63 g, 98%)

Sources & evidence

ORD record
ord-19d16a55e1f74b0e8f7aa744cd73cf60
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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