Dimethylformamide → HCID 68782388, compound

HRID 2266533Notes

Reaction equation

HRID 2266533 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([CH3:36])=[C:9]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1)[C:10](OS(C(F)(F)F)(=O)=O)=[N:11]2.[Cl-].[Li+].[CH3:40][N:41](C)C=O>O.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([CH3:36])=[C:9]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:33])=[O:34])=[CH:28][CH:27]=1)[C:10]([C:40]#[N:41])=[N:11]2

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 433294Lithium ChlorideHCID 86631443HCID 86631443, compound

Product 1

HCID 68782388HCID 68782388, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of [8-chloro-3-(4-methanesulfonylbenzyl)-4-methyl-2-trifluoromethanesulfonyloxyquinolin-5-yloxy]acetic acid methyl ester, (0.080 g), zinc cyanide (0.010 g), tetrakis(triphenylphosphine)palladium(0) (0.030 g), and lithium chloride (0.001 g) in N,N-dimethylformamide (8.0 mL) was heated by microwave irradiation at 120° C. for 15 minutes. The mixture was diluted with water and the resulting precipitate collected by filtration, washed with water and diethyl ether and then dried to afford title compound, 0.056 g.

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. washwashed with water and diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-8df4c0fbffff46208f24251242513e7b
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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