Diglyme → 1-[2,6-Dichloro4-(4-trifluoromethylphenyl)phenyl]-3-cyano-4-trifluoromethylthio-5-aminopyrazole

HRID 1066199Notes

Reaction equation

[NH:1]([C:8]1[N:12]([C:13]2[C:18]([Cl:19])=[CH:17][C:16](Br)=[CH:15][C:14]=2[Cl:21])[N:11]=[C:10]([C:22]#[N:23])[C:9]=1[S:24][C:25]([F:28])([F:27])[F:26])C1C=CC=CC=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+].COCCOCCOC>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.O>[Cl:21][C:14]1[CH:15]=[C:16]([C:34]2[CH:35]=[CH:36][C:31]([C:30]([F:41])([F:40])[F:29])=[CH:32][CH:33]=2)[CH:17]=[C:18]([Cl:19])[C:13]=1[N:12]1[C:8]([NH2:1])=[C:9]([S:24][C:25]([F:28])([F:26])[F:27])[C:10]([C:22]#[N:23])=[N:11]1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 6 g of 5-amiino-3-cyano-1-(2,6-dichloro-4-bromophenyl)-4-trifluoromethylthiopyrazole (prepared according to procedures reported in U.S. Pat. No. 5,232,940), 4-trifluoromethylphenylboronic acid (5.3 g), K2CO3 (5.8 g), tris-(dibenzylidene acetone) dipalladium (0.6 g) and diglyme was heated at 130° C. for 25 hours. After cooling to 20° C., the mixture was poured into water and extracted with diethyl ether. The ether solutions were combined, dried, filtered and the filtrate concentrated and purified by chromatography. The desired product as a solid (3.9 g, mp 181-184° C.) was obtained.

Workup

customprepared
extractionextracted with diethyl ether
customdried
filtrationfiltered
concentrationthe filtrate concentrated
custompurified by chromatography

Sources & evidence

ORD record: ord-ec6b699d5a9f4790b71052e7506a4beb
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06242475B1

Reaction notes

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