Dichloromethane → HCID 67410900, compound

HRID 1191171Notes

Reaction equation

HRID 1191171 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[N:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1Br)=[O:5])[CH3:2].[C:17]([Cu])#[N:18].C(Cl)Cl>CN1C(=O)CCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[N:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[C:17]#[N:18])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 147933444-bromo-5-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid ethyl esterHCID 178418546HCID 178418546, compound

Product 1

HCID 67410900HCID 67410900, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4-bromo-5-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (1.00 g, 3.46 mmol) and CuCN (372 mg, 4.15 mmol) in NMP (10 mL) was stirred at 200° C. under microwave irradiation for 1 h. After cooling to room temperature, the mixture was treated with DCM (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (0:100-10:90 EtOAc-hexanes) to yield the title compound as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 4.45 (q, J=7.2 Hz, 2H), 4.14 (s, 3H), 1.45 (t, J=7.2 Hz, 3H), 1.43 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated For C12H17N3O2: 236.1 (M+H), Measured: 236.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography on silica gel (0:100-10:90 EtOAc-hexanes)

Sources & evidence

ORD record
ord-e893512921fb4885bd373b6da5b37fa3
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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