HCID 57494744, compound → HCID 57444746, compound

HRID 861150Notes

Reaction equation

HRID 861150 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:10]([CH:11]=[O:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1.[C:21]([Mg]Br)#[CH:22]>>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:10]([CH:11]([OH:12])[C:21]#[CH:22])=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 57494744HCID 57494744, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 57444746HCID 57444746, compoundYield 94%

Procedure

In a similar manner as described in Example 46 from 7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (5.11 g, 17.8 mmol) and ethynylmagnesium bromide (89 mL, 0.5 M in tetrahydrofuran, 44.6 mmol) at 0° C. was obtained 1-[7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-ol (5.22 g, 94%) as an off-white solid. 1H NMR (CDCl3): δ 8.02 (d, 1 H), 7.73 (d, 2 H), 7.18 (t, 1 H), 7.02 (d, 2 H), 6.97 (d, 1 H), 5.79 (m, 1 H), 3.87 (s, 3 H), 2.68 (m, 1 H), 2.25 (d, 1H).

Sources & evidence

ORD record
ord-c9d15cca4f9d4371b9981f608ce05de8
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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