Dimethylformamide → HCID 71532820, compound

HRID 2274955Notes

Reaction equation

HRID 2274955 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[C:12]3[CH2:13][N:14]([C:17](=[O:19])[CH3:18])[CH2:15][CH2:16][C:11]=3[N:10]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[N:9]=2)[CH:3]=1.[CH3:29][N:30](C)C=O>COC(C)(C)C.[C-]#N.[C-]#N.[Zn+2].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>[C:17]([N:14]1[CH2:15][CH2:16][C:11]2[N:10]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[N:9]=[C:8]([C:4]3[CH:3]=[C:2]([CH:7]=[CH:6][N:5]=3)[C:29]#[N:30])[C:12]=2[CH2:13]1)(=[O:19])[CH3:18]

Participants

6

Reactant 2

HCID 6228Dimethylformamide2×HCID 71533245HCID 71533245, compound

Product 1

HCID 71532820HCID 71532820, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of Zn(CN)2 (39 mg, 0.335 mmol) and tetrakis(triphenylphosphine)palladium(0) (19 mg, 0.016 mmol) in dry N,N-dimethylformamide (0.6 ml) at 150° C. was slowly added a solution of 1-[3-(4-Bromo-pyridin-2-yl)-1-(2,4-difluoro-benzyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone (6j) (0.15 g, 0.335 mmol) in dry N,N-dimethylformamide (1 ml). The mixture was stirred at 150° C. for 3 h and then at 25° C. for 16 h. The mixture was diluted with methyl-tert-butylether, filtrated over Celite, washed with water, dried over Na2SO4, filtrated and evaporated to dryness. The residue was suspended in methanol, and the solid was filtrated off to give 67 mg of 2-[5-Acetyl-1-(2,4-difluoro-benzyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-isonicotinonitrile (13a).

Workup

  1. waitat 25° C. for 16 h
  2. filtrationfiltrated over Celite
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltrated
  6. customevaporated to dryness
  7. filtrationthe solid was filtrated off

Sources & evidence

ORD record
ord-8fefb17cded3409e8f3bd602cb16d876
Source dataset
uspto-grants-2015_09
Patent number
US09127001B2

Reaction notes

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