1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(2-(4-Methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one

HRID 731701Notes

Reaction equation

HRID 731701 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1.[I-].[NH2:17][N+:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1CCN2C(=NCCC2)CC1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:11](=[O:15])[CH:12]([CH3:13])[CH3:14])=[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]3[N:17]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 685422801-(4-Methoxyphenyl)-4-methyl-1-pentyn-3-one

Product 1

HCID 578375001-(2-(4-Methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-oneYield 45%

Procedure

Starting with 5.0 g (36.7 mmol) of 4-methoxyethynylbenzene, 3.85 ml of isobutyryl chloride, and 5.0 g ZnCl2, the corresponding 1-(4-methoxyphenyl)-4-methylpent-1-yn-3-one was prepared using the same procedure as in Example 5(a) to obtain 7.87 g of crude oil intermediate. Starting with 7.5 g (37 mmol) of 1-(4-methoxyphenyl)-4-methylpent-1-yn-3-one, 8.22 g (37 mmol) of 1-aminopyridinium iodide and 11.6 g DBU, 4.84 g (45%) of 1-(2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one was obtained as in Example 5(b). Compound 1021.

Sources & evidence

ORD record
ord-16e21e456b3e4181b7442ff611ec6b72
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

Loading…