Sodium hydride → HCID 59295418, compound

HRID 2233308Notes

Reaction equation

HRID 2233308 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:19]2[CH:20]=[N:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=2)[S:15][C:16]=1[CH2:17][OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl:31][C:32]1[CH:39]=[C:38](F)[CH:37]=[CH:36][C:33]=1[C:34]#[N:35]>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:19]2[CH:20]=[N:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=2)[S:15][C:16]=1[CH2:17][O:18][C:38]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[C:32]([Cl:31])[CH:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1090002-Chloro-4-fluorobenzonitrileHCID 59295434HCID 59295434, compound

Product 1

HCID 59295418HCID 59295418, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.44 g [4-(3-Benzyloxy-propyl)-2-(6-trifluoromethyl-pyridin-3-yl)-thiazol-5-yl]-methanol were dissolved in 15 ml dimethylformamide. 231 mg sodium hydride (95%) were added and the reaction mixture stirred at room temperature. After thirty minutes 549 mg 2-chloro-4-fluorobenzonitrile were added and the reaction mixture stirred at room temperature for one hour. Then the reaction was quenched by the addition of 20 ml water and extracted three times with portions of 50 ml methyltertbutylether. The combined organic phases were dried over MgSO4. The solvent was removed in vacuo. The resulting residue was purified by reversed phase HPLC to obtain 641 mg 4-[4-(3-Benzyloxy-propyl)-2-(6-trifluoromethyl-pyridin-3-yl)-thiazol-5-ylmethoxy]-2-chloro-benzonitrile as yellow lyophilisate.

Workup

  1. stirringthe reaction mixture stirred at room temperature for one hour
  2. customThen the reaction was quenched by the addition of 20 ml water
  3. extractionextracted three times with portions of 50 ml methyltertbutylether
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customThe resulting residue was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-4b2dd12960184599a9491b960658d65c
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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