Dimethylformamide → HCID 178510329, compound

HRID 2218404Notes

Reaction equation

HRID 2218404 reaction equation
Cl[C:2]1[C:3]([Cl:26])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[CH3:27][N:28](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].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.[Fe+2].CCOC(C)=O>[Cl:26][C:3]1[C:2]([C:27]#[N:28])=[CH:7][N:6]=[C:5]2[NH:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:13][CH:12]=3)=[N:10][C:4]=12

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 178478272HCID 178478272, compound

Product 1

HCID 178510329HCID 178510329, compoundYield 24%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

6,7-Dichloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-3H-imidazo[4,5-b]pyridine (Example 206) (0.063 g, 0.16 mmol), Zn(CN)2 (0.018 g, 0.153 mmol), Pd2(dba)3 (0.036 g, 0.039 mmol) and dppf (0.036 g, 0.065 mmol) were mixed in a vial. DMF (6 ml) was added and the reaction mixture was heated to 120° C. under argon for 3 h. EtOAc (50 ml) was added and the solution was washed with water. Drying (Na2SO4) and evaporation delivered crude material which was purified by HPLC-C18, giving the title product (0.015 g, 24%).

Workup

  1. washthe solution was washed with water
  2. customDrying
  3. custom(Na2SO4) and evaporation
  4. customwas purified by HPLC-C18

Sources & evidence

ORD record
ord-35cfc17f2a50480ab670cbaf4accb1dc
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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