Methanol → ethyl 3-tert-butyl-1-(2-(dimethylamino)ethyl)-1H-pyrazole-5-carboxylate

HRID 217880Notes

Reaction equation

HRID 217880 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:23][CH2:24][N:25]([CH3:27])[CH3:26].CO>C(Cl)Cl.CCOC(C)=O>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 2743509Ethyl 3-tert-butyl-1H-pyrazole-5-carboxylateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 59588870ethyl 3-tert-butyl-1-(2-(dimethylamino)ethyl)-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Method I was used with ethyl 3-tert-butyl-1H-pyrazole-5-carboxylate (124 mg, 0.632 mmol), caesium carbonate (624 mg, 1.915 mmol) and 2-chloro-N,N-dimethylethanamine hydrochloride (96.8 mg, 0.672 mmol). 48 hours reaction time. Column eluent: 50→100% EtOAc in CH2Cl2, followed by 0→10% MeOH in EtOAc. Yield: 103 mg (61%) of a colorless oil.

Workup

  1. custom48 hours reaction time

Sources & evidence

ORD record
ord-5e98ecde5339450aa5a3e09831e0e430
Source dataset
uspto-grants-2012_06
Patent number
US08198279B2

Reaction notes

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