4-(4-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)-2-chlorobenzonitrile → 5-(3-chloro-4-cyanophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbonitrile

HRID 872870Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][N:5]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[C:6]=1[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([Cl:15])[CH:8]=1.[Cu][C:23]#[N:24]>CN(C)C=O>[Cl:15][C:9]1[CH:8]=[C:7]([C:6]2[N:5]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[N:4]=[CH:3][C:2]=2[C:23]#[N:24])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12]

Participants

Conditions

Temperature: 190 °C

Procedure

4-(4-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)-2-chlorobenzonitrile (3 g, 8.18 mmol), copper(I) cyanide (0.733 g, 8.18 mmol) and N,N-dimethyl formamide (15 ml) were loaded in a microwave reactor tube. The mixture was heated 190° C. for 5 h. The reaction was quenched by pouring the mixture into 200 ml of 12% ammonia solution and stirred for 30 min. The precipitate was filtered, washed with water and dried in vacuum at 40° C. The product was used in the next step without further purification. LC-MS: [M+1]=313.75.

Workup

customThe reaction was quenched
additionby pouring the mixture into 200 ml of 12% ammonia solution
filtrationThe precipitate was filtered
washwashed with water
customdried in vacuum at 40° C
customThe product was used in the next step without further purification

Sources & evidence

ORD record: ord-ecbba8d88fd54c86be3c9a330948d8bd
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975254B2

Reaction notes

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