Sodium hydride → HCID 64429562, compound

HRID 254003Notes

Reaction equation

HRID 254003 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[N:6][NH:7][CH:8]=1.Cl[CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>CN(C=O)C>[I:3][C:4]1[CH:5]=[N:6][N:7]([CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 770224-IodopyrazoleHCID 816691-(2-Chloroethyl)pyrrolidine

Product 1

HCID 64429562HCID 64429562, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (60% paraffin oil dispersion, 0.507 g, 21.13 mmol) was added portionwise to a solution of 4-iodopyrazole in DMF at 0° C. The reaction mixture was stirred for 1 hour, treated with solution of 1-(2-chloroethyl)pyrrolidine (1.40 g, 10.56 mmol) in DMF, slowly warmed to RT and stirred for additional 16 hours. The reaction mixture was cooled to 0° C. and ice cold water was added, followed by extraction with EtOAc (2×40 mL). The combined organics were washed with water (3×40 mL), brine solution (40 ml), dried (Na2SO4), filtered, and concentrated to obtain 4-iodo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrazole, which was used as is for subsequent reactions without further purification; 1H-NMR (400 MHz, CHCl3): 7.60 (1H, s), 7.52 (1H, s), 7.49 (1H, s), 4.25 (2H, t), 2.95 (2H, s), 2.57 (4H, m), 1.79 (4H, m); ES-MS: 292.0 (M+H).

Workup

  1. stirringstirred for additional 16 hours
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. additionice cold water was added
  4. extractionfollowed by extraction with EtOAc (2×40 mL)
  5. washThe combined organics were washed with water (3×40 mL), brine solution (40 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-25154bb00de14012a23b38cb03e0c2e3
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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