Dimethylformamide → HCID 57654567, compound

HRID 1921658Notes

Reaction equation

HRID 1921658 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([C:17]([F:29])([F:28])[C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[N:24]=[CH:23][CH:22]=[CH:21]5)=[N:15][N:16]=3)[N:13]=2)[CH:5]=[CH:4][N:3]=1.[CH3:30][N:31](C=O)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>[F:28][C:17]([F:29])([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][CH:22]=[CH:21]2)[C:14]1[N:12]2[N:13]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:30]#[N:31])[CH:7]=3)[CH:9]=[CH:10][C:11]2=[N:16][N:15]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 57654521HCID 57654521, compound

Product 1

HCID 57654567HCID 57654567, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of 6-{[6-(2-Chloro-pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]-difluoro-methyl}-quinoline (see Example 100b) (50 mg, 0.122 mmol) in DMF (4 mL) and Zn(CN)2 (43 mg, 0.367 mmol) was degassed with house vacuum for ˜5 min, and tetrakis(triphenylphosphine)palladium (13.4 mg, 0.012 mmol) were then added. The mixture was microwaved at 190° C. for 20 min. Following the aqueous work up, solvent was removed by vacuo. The target compound, 211 mg (41%), was obtained by column purification. 1H NMR (CDCl3) δ 9.04 (dd, J=4.2, 1.6 Hz, 1H), 8.95 (d, J=5.12 Hz, 1H), 8.41 (d, J=9.8 Hz, 1H), 8.22-8.35 (m, 4H), 8.00-8.05 (m, 2H), 7.70 (d, J=9.8 Hz, 1H), 7.54 (dd, J=8.2, 3.8 Hz, 1H); MS (ES) m/z 400.3 (M+H+).

Workup

  1. customwas degassed with house vacuum for ˜5 min
  2. customThe mixture was microwaved at 190° C. for 20 min
  3. customsolvent was removed by vacuo
  4. customThe target compound, 211 mg (41%), was obtained by column purification

Sources & evidence

ORD record
ord-7f479afb83444d4d97b4e009b69a951e
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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