Water → HCID 54227958, compound

HRID 2268903Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][N:18]=[CH:17][C:16]=2[Cl:22])=[N:4][N:3]=1.[C:23]([O-:26])([O-])=[O:24].[K+].[K+].[CH:29]1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>CS(C)=O.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:29][O:26][C:23]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][N:18]=[CH:17][C:16]=2[Cl:22])=[N:4][N:3]=1)=[O:24]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 4-chloro-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine (9.7 g, 27 mmoles), prepared as described in example 45, in DMSO/CH3OH (80/40 ml) was added with K2CO3 (7.4 g, 54 mmoles), palladium acetate (0.31 g, 1.4 mmoles) and 1,3-bis(diphenylphosphine)propane (0.75 g, 1.82 mmoles). The mixture was placed in autoclave under CO atmosphere (8 bar) and heated at 50° C. After 4 hours the mixture was poured into water (10 volumes) and extracted four times with ethyl acetate. The organic phase was washed with aqueous NaCl and discoloured with charcoal, filtered and dried to give a solid which was flash chromatographed (eluent: petrolatum/ethyl acetate 1:1) to give 5 g of the title compound (yield: 49%).

Workup

customprepared
extractionextracted four times with ethyl acetate
washThe organic phase was washed with aqueous NaCl
filtrationfiltered
customdried
customto give a solid which
customchromatographed (eluent: petrolatum/ethyl acetate 1:1)

Sources & evidence

ORD record: ord-7272da4756d04612839e2bc5f483de83
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329370B1

Reaction notes

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