Dimethylformamide → HCID 11299938, compound

HRID 1860234Notes

Reaction equation

HRID 1860234 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][N:3]=1.[CH3:20][N:21](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:14]1([CH2:13][O:12][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([C:20]#[N:21])=[N:3][CH:4]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 11173252HCID 11173252, compound

Product 1

HCID 11299938HCID 11299938, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
150 °C

Procedure

A mixture of 1-chloro-4-(phenylmethoxy)isoquinoline (2.26 g, 8.4 mmol), Zn(CN)2 (590 mg), tris(dibenzylideneacetone)dipalladium (219 mg), 1,1′-bis(diphenylphosphino)ferrocene (270 mg) in 100 ml of DMF is heated at 150° C. for 24 h under nitrogen. TLC and LC-MS analysis indicates complete consumption of starting material after 24 h. The mixture is then cooled to 80° C. and gradually diluted with 4:1:4 saturated aq. NH4Cl: concentrated NH4OH:water (200 mL) over 0.5 hours. The slurry is cooled to 0° C. and filtered through celite. The tan solid is collected by filtration, washed and dried to give the titled compound as a tan solid (1.5 g), m.p. 124-125° C.

Workup

  1. customconsumption of starting material after 24 h
  2. temperatureThe mixture is then cooled to 80° C.
  3. additiongradually diluted with 4:1:4 saturated aq. NH4Cl
  4. temperatureThe slurry is cooled to 0° C.
  5. filtrationfiltered through celite
  6. filtrationThe tan solid is collected by filtration
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-3c6b529287bc49f8a79d705c0bbf5e93
Source dataset
uspto-grants-2003_03
Patent number
US06528649B2

Reaction notes

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