Water → HCID 18332464, compound

HRID 2268906Notes

Reaction equation

HRID 2268906 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.[K+].[K+].C1(P([C:42]2[CH:47]=[CH:46]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[Cl:22][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:21])[C:15]=1[CH2:14][C:5]1[C:6]2[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[C:2]([C:42]#[C:47][CH2:46][N:18]2[CH2:19][CH2:23][O:26][CH2:16][CH2:17]2)=[N:3][N:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 186292104-Chloro-1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxyphthalazine

Product 1

HCID 18332464HCID 18332464, compoundYield 1,179.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution under N2 of 4-chloro-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine (1.3 g, 3.7 mmoles), prepared as described in example 45, in dry DMF (50 ml) was added with K2CO3 (1.28 g, 9.25 mmoles), palladium acetate (0.017 g, 0.074 mmoles), CuI (0.028 g, 0.15 mmoles), and triphenylphosphine (0.58 g, 0.22 mmoles). After 30 minutes under stirring 4-prop-2-ynyl-morpholine (1.16 g, 9.25 mmoles) was added and the mixture was stirred overnight, poured into water (10 volumes) and extracted twice with ethyl acetate. After decolouring with charcoal, filtering over celite, concentrating and triturating in ethyl ether, 1.15 g of the title compound were obtained (yield: 70%). m.p.: 171.7-172.7° C. (dec.).

Workup

  1. additionAfter 30 minutes under stirring 4-prop-2-ynyl-morpholine (1.16 g, 9.25 mmoles) was added
  2. extractionextracted twice with ethyl acetate
  3. filtrationfiltering over celite
  4. concentrationconcentrating
  5. customtriturating in ethyl ether

Sources & evidence

ORD record
ord-9b4171c35cc046debf3c40e24790db32
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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