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

HRID 731704Notes

Reaction equation

HRID 731704 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[I-].[NH2:16][N+:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1CCN2C(=NCCC2)CC1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:10](=[O:14])[CH:11]([CH3:12])[CH3:13])=[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 685456841-(4-Chlorophenyl)-4-methylpent-1-yn-3-one

Product 1

HCID 578374761-(2-(4-Chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-oneYield 43.4%

Procedure

Starting with 4.9 g (35.8 mmol) of 4-chloroethynylbenzene, 3.76 ml of isobutyryl chloride and 4.88 g ZnCl2, the corresponding 1-(4-chlorophenyl)-4-methylpent-1-yn-3-one was prepared using the same procedure as in Example 5(a) to obtain 9.21 g of crude oil intermediate. Starting with 9.21 g (35.8 mmol) of 1-(4-chlorophenyl)-4-methylpent-1-yn-3-one, 9.90 g (44 mmol) of 1-aminopyridinium iodide and 11 g DBU, the desired product was obtained—4.64 g (43%) of 1-(2-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one as in Example 5(b). Compound 1024.

Sources & evidence

ORD record
ord-ae5d54edaa994d16874466c6928efefc
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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