Methanol → HCID 18326242, compound

HRID 1250438Notes

Reaction equation

[Cl:1][C:2]1[C:7](I)=[CH:6][C:5]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]#[N:16])[N:11]([CH3:17])[N:10]=2)=[C:4]([F:18])[CH:3]=1.[CH3:19][OH:20].[C]=[O:22].C(N([CH2:28][CH3:29])CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:19]([O:22][CH2:28][CH3:29])=[O:20])=[CH:6][C:5]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]#[N:16])[N:11]([CH3:17])[N:10]=2)=[C:4]([F:18])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5.2 g of 3-(4-chloro-2-fluoro-5-iodophenyl)-4-methyl-5-cyano-1-methyl-[1H]-pyrazole (Example H8), 60 ml of methanol, 2.8 g of triethylamine and 0.4 g of bis(triphenylphosphine)palladium(II) dichloride (PdCl2(PPh3)2) are placed into a 100 ml pressurized container and stirred for 16 hours at a temperature of 100° C. and a carbon monoxide pressure of 10 megapascal (Mpa). The solvent is subsequently evaporated and the crude product which remains is purified over a silica gel column (eluent: ethyl acetate/hexane 1/5). This gives 3.1 g (69.3% of theory) of the desired product.

Workup

customThe solvent is subsequently evaporated
customthe crude product which remains is purified over a silica gel column (eluent: ethyl acetate/hexane 1/5)

Sources & evidence

ORD record: ord-aad0531215d84836ba9ef4c1ca22ba7a
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06339046B1

Reaction notes

Loading…