1,3-Thiazol-2-ylmethanol → Ethyl 5-trifluoromethyl-1-[(thiazol-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 1804741Notes

Reaction equation

HRID 1804741 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9][C:6]2=[N:7][CH:8]=1.[S:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH2:24]O.C(C=P(CCCC)(CCCC)CCCC)#N>>[F:18][C:2]([F:1])([F:17])[C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:9]([CH2:24][C:20]3[S:19][CH:23]=[CH:22][N:21]=3)[C:6]2=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 27952131,3-Thiazol-2-ylmethanolHCID 4622928CyanomethylenetributylphosphoraneHCID 60146028ethyl 5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Product 1

HCID 66845785Ethyl 5-trifluoromethyl-1-[(thiazol-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylateYield 83.1%

Procedure

This compound was prepared according to a process similar to that described in step 5.1. by reacting 390 mg (1.51 mmol) of ethyl 5-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (WO2008/107543) with 348 mg (3.02 mmol) of thiazol-2-ylmethanol in the presence of 0.92 g (3.826 mmol) of (cyanomethylene)-tributylphosphorane (CMBP). The reaction mixture is then purified by flash chromatography on a column of silica gel in a mixture of heptane and ethyl acetate to give 446 mg of the expected product in the form of an oil.

Workup

  1. customThis compound was prepared
  2. customThe reaction mixture is then purified by flash chromatography on a column of silica gel in a mixture of heptane and ethyl acetate

Sources & evidence

ORD record
ord-04bccdf9afdc474a9d9ff083ab0e6c6c
Source dataset
uspto-grants-2013_01
Patent number
US08354425B2

Reaction notes

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