Dimethylformamide → HCID 22030088, compound

HRID 968622Notes

Reaction equation

HRID 968622 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[NH2:18].[Cl-].[NH4+].[OH-].[NH4+].C[N:24]([CH:26]=[O:27])C>O.[C-]#N.[Zn+2].[C-]#N.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]>[NH2:18][C:3]1[C:2]([C:26]([NH2:24])=[O:27])=[N:7][CH:6]=[C:5]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:4]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 220300306'-Chloro-3-(trifluoromethyl)[2,3'-bipyridin]-5'-amine

Product 1

HCID 22030088HCID 22030088, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

Heat a solution of 6′-chloro-3-trifluoromethyl-[2,3′]bipyridinyl-5′-ylamine (25 g, 0.091 mol), zinc cyanide (6.75 g, 0.058 mol), tris[dibenzylidineacetone]di-palladium (pd2(dba)3; 2.63 g, 2.86 mmol), and 1,1′-bis(diphenylphosphino)ferrocene (DPPF; 3.16 g, 5.72 mmol) in DMF (250 mL) and water (2.5 mL), under a nitrogen atmosphere, at 120° C. for 1 hour. Add water (30 mL) and heat the solution at 120° C. for a further 4 hours to complete the hydrolysis. Cool the reaction to 0° C. and add a solution of saturated ammonium chloride (200 ml), water (200 mL) and concentrated ammonium hydroxide (50 mL). After stirring at 0° C. for 1 hour, filter the yellow precipitate, and wash with water (200 mL) and a 1:1 mixture of ether-hexane (200 mL). Air dry the solid, and then dry in a vacuum oven to give (23 g, 90%) of the title compound.

Workup

  1. customthe hydrolysis
  2. temperatureCool
  3. customthe reaction to 0° C.
  4. filtrationfilter the yellow precipitate
  5. washwash with water (200 mL)
  6. additiona 1:1 mixture of ether-hexane (200 mL)
  7. customAir dry the solid
  8. customdry in a vacuum oven

Sources & evidence

ORD record
ord-acdb2cde83024ead93372e25247c2595
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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