Dimethylformamide → HCID 57814375, compound

HRID 2383249Notes

Reaction equation

HRID 2383249 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:7][CH2:6][N:5]2[CH:8]=[N:9][CH:10]=[C:4]2[CH:3]1[C:11]1[CH:16]=[CH:15][C:14](OS(C(F)(F)F)(=O)=O)=[CH:13][CH:12]=1.[CH3:26][N:27](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][C:2]1([CH3:25])[CH2:7][CH2:6][N:5]2[CH:8]=[N:9][CH:10]=[C:4]2[CH:3]1[C:11]1[CH:16]=[CH:15][C:14]([C:26]#[N:27])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86650601HCID 86650601, compound

Product 1

HCID 57814375HCID 57814375, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
120 °C

Procedure

1.03 mmol of trifluoromethanesulphonic acid 4-(7,7-dimethyl-5,6,7,8-tetrahydroimidazo-[1,5-a]pyridin-8-yl)phenyl ester and 2.06 mmol of zinc(II) cyanide are introduced under argon in 10 ml of absolute N,N-dimethylformamide. The reaction mixture is admixed with 0.05 mmol of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium and stirred at 120° C. for 20 hours. The reaction mixture is poured into ice-water and extracted with tert-butyl methyl ether (3×). The combined organic phases are dried with magnesium sulphate and evaporated. From the residue the title compound is obtained by means of flash chromatography (SiO2 60 F) as a pale pink solid. Rf=0.17 (dichloromethane/ammonia (2M in EtOH) 97:3), Rf=5.40 (Gradient I).

Workup

  1. extractionextracted with tert-butyl methyl ether (3×)
  2. dry with materialThe combined organic phases are dried with magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-55df5159b3204f40a00bc6071a0f4c16
Source dataset
uspto-grants-2012_09
Patent number
US08263615B2

Reaction notes

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