Cesium carbonate → HCID 18008971, compound

HRID 987513Notes

Reaction equation

HRID 987513 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[N:4]([C:8]2[C:17]([F:18])=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[N:3]=1.Br[CH2:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][CH2:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[N:4]([C:8]2[C:17]([F:18])=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 869964-(Bromomethyl)benzonitrileHCID 18008982HCID 18008982, compound

Product 1

HCID 18008971HCID 18008971, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To the mixture of 3-methyl-1-(3-fluoro-2-naphthyl)-5-amino-1H-pyrazole (200 mg, 0.48 mmol) and 4-bromomethylbenzonitrile (140 mg, 0.72 mmol) in 5 mL DMF was added Cs2CO3 (234 mg, 0.72 mmol). The mixture was stirred for overnight at 50° C. It was diluted with 200 mL EtOAc, washed with water ×2, dried, evaporated in vacuuo, purified using flash column to afford 3-methyl-1-(3-fluoro-2-naphthyl)-5-((4-cyanophenyl)methylamino)-1H-pyrazole. ES-MS: (M+H)+357.

Workup

  1. washwashed with water ×2
  2. customdried
  3. customevaporated in vacuuo
  4. custompurified

Sources & evidence

ORD record
ord-97ce86efa5c844a08243113dc00b9b14
Source dataset
uspto-grants-2003_10
Patent number
US06632815B2

Reaction notes

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