Triethylamine → HCID 68838020, compound

HRID 660495Notes

Reaction equation

HRID 660495 reaction equation
[C:1](Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[I:12][C:13]1[CH:14]=[N:15][NH:16][CH:17]=1.CCN(CC)CC>C1(C)C=CC=CC=1>[CH2:4]([O:3][C:1]([N:15]1[CH:14]=[C:13]([I:12])[CH:17]=[N:16]1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 770224-Iodopyrazole

Product 1

HCID 68838020HCID 68838020, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

CbzCl (95% grade, 2.9 mL, 20 mmol) is added to a solution of 4-iodo-1H-pyrazole (2.97 g, 15.3 mmol) and Et3N (3.2 mL, 23 mmol) in toluene (30 mL) at 0° C. The mixture is stirred at 0° C. for 1 h and partitioned between EtOAc and aq. NaHCO3. The organic layer is dried over MgSO4, concentrated and chromatographed to afford the title compound as a white solid: 1H NMR (CDCl3) δ 8.20 (s, 1H), 7.72 (s, 1H), 7.50-7.31 (m, 5H), 5.46 (s, 2H).

Workup

  1. custompartitioned between EtOAc and aq. NaHCO3
  2. dry with materialThe organic layer is dried over MgSO4
  3. concentrationconcentrated
  4. customchromatographed

Sources & evidence

ORD record
ord-cd850876858148409ba2169b2a44e18e
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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