Dimethylformamide → 5-Chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde

HRID 1062873Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH:10]=[C:4]2[CH:3]=1.P(Cl)(Cl)(Cl)=O.CN(C)[CH:26]=[O:27]>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[C:10]([CH:26]=[O:27])=[C:4]2[CH:3]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24813Phosphorus oxychloride

HCID 221809255-Chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine

Product 1

HCID 221809165-Chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde

Procedure

5-Chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine (1.0 g, 3.86 mmol) was treated with N,N-dimethylformamide (20 mL) and phosphorous oxychloride (0.54 mL, 7.8 mmol) as described in Example 12 to give 5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde as a white crystalline solid, (0.9 g, 81%). 1H NMR (CDCl3): δ 10.12 (s, 1H), 8.52 (d, 1H), 8.47 (d, 1H), 7.76 (d, 2H), 7.11-7.06 (m, 3H), 3.93 (s, 3H); MS m/z 287 (M+1).

Sources & evidence

ORD record: ord-c29049a4a3a84aeca4a10603faae43ab
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06962914B2

Reaction notes

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