N-methyl-2-pyrrolidone → HCID 71272741, compound

HRID 475159Notes

Reaction equation

HRID 475159 reaction equation
Br[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1.[CH3:21][N:22]1C(=O)CCC1>[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>[O:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH:15]1[N:6]1[C:7]2[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:2]([C:21]#[N:22])[C:3]=2[CH:4]=[N:5]1

Participants

5

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 71272199HCID 71272199, compound

Product 1

HCID 71272741HCID 71272741, compoundYield 79%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
85 °C

Procedure

A sealed-cap vial was charged with 4-bromo-1-(tetrahydro-2H-pyran-2-yl)-6-(trifluoromethyl)-1H-indazole (1.03 g, 2.95 mmol), Zn(CN)2 (0.38 g, 3.24 mmol), Pd(PPh3)4 (0.24 g, 0.21 mmol), and NMP (8 mL). The mixture was degassed for 5 min under nitrogen and the mixture then stirred under nitrogen at 85° C. for 16 h. The mixture was filtered and the filtrate concentrated in vacuo. The crude mixture was purified by SiO2 chromatography to afford 1-(tetrahydro-2H-pyran-2-yl)-6-(trifluoromethyl)-1H-indazole-4-carbonitrile as a solid (0.69 g, 79%). MS (ESI) m/z: 296.3 [M+1]+.

Workup

  1. customThe mixture was degassed for 5 min under nitrogen
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe crude mixture was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-8f78909afdb344c085e52f0f21cf4d21
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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