Ethyl bromoacetate → HCID 57899083, compound

HRID 76052Notes

Reaction equation

HRID 76052 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4([OH:28])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:37]([O:39][C:40](=[O:43])[CH2:41]Br)[CH3:38]>CN(C=O)C>[CH2:37]([O:39][C:40](=[O:43])[CH2:41][N:25]1[CH2:24][CH2:23][C:22]([OH:28])([C:19]2[CH:18]=[CH:17][C:16]([C:13]3[CH:14]=[N:15][C:10]([NH:9][C:6]4[CH:7]=[N:8][C:3]([C:2]([F:1])([F:29])[F:30])=[CH:4][CH:5]=4)=[CH:11][CH:12]=3)=[CH:21][CH:20]=2)[CH2:27][CH2:26]1)[CH3:38]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 666158914-{4-[6-(6-Trifluoromethyl-pyridin-3-ylamino)-pyridin-3-yl]-phenyl}-piperidin-4-ol

Product 1

HCID 57899083HCID 57899083, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{4-[6-(6-Trifluoromethyl-pyridin-3-ylamino)-pyridin-3-yl]-phenyl}-piperidin-4-ol (153 mg, 0.37 mmol, prepared by analogous procedures described above) was dissolved in DMF (2 mL) and to it was added K2CO3 (128 mg, 0.93 mmol) followed by bromo-acetic acid ethyl ester (0.050 mL, 0.44 mmol) added dropwise, and the reaction was stirred for 18 hours. The reaction mixture was partitioned between 40% EtOAc/hexanes and water, washed with brine, dried with magnesium sulfate, filtered, and concentrated via rotary evaporation to obtain the title compound as a crude oil, which was taken to the next step without purification: MS (M+H)+499.4.

Workup

  1. additionadded dropwise
  2. customThe reaction mixture was partitioned between 40% EtOAc/hexanes and water
  3. washwashed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-ec9b82d36fb64fd1982132cc49ad44d7
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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