Pyrazole → HCID 68910663, compound

HRID 1962673Notes

Reaction equation

HRID 1962673 reaction equation
CS(OCCC(N1C=C([C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH:22]=[CH:23][C:16]=23)C=N1)C)(=O)=O.[NH:32]1[CH:36]=[CH:35][CH:34]=[N:33]1.C[N:38]([CH:40]=O)C.[H-].[Na+]>>[CH3:17][CH:16]([C:23]1([C:22]2[N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:30])[CH3:31])[C:17]3=[N:18][CH:19]=[CH:20][CH:15]=[C:16]3[CH:23]=2)[CH2:40][NH:38][N:21]=[CH:22]1)[CH2:15][CH2:20][C:35]1[CH:36]=[N:32][NH:33][CH:34]=1

Participants

5

Reactant 4

HCID 1048PyrazoleHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 57477568HCID 57477568, compound

Product 1

HCID 68910663HCID 68910663, compoundYield 87%

Procedure

To a 0° C. solution of 3-[4-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]butyl methanesulfonate (prepared by mesylation of the alcohol as in Example 59, Step 1) (0.055 g, 0.00012 mol) and 1H-pyrazole (0.025 g, 0.00036 mol) in DMF (1 mL, 0.01 mol) was added sodium hydride (0.014 g, 0.00036 mol). The resulting solution was stirred overnight and then partitioned between ethyl acetate and 0.1 N HCl, water. The organic phase was separated and washed with brine. The organic layer was then concentrated to give 49 mg of a pale orange glass (87% yield).

Workup

  1. custompartitioned between ethyl acetate and 0.1 N HCl, water
  2. customThe organic phase was separated
  3. washwashed with brine
  4. concentrationThe organic layer was then concentrated

Sources & evidence

ORD record
ord-42ec3a49e129492d8726a91cfd4bc20b
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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