Chloroacetaldehyde → HCID 67000913, compound

HRID 558613Notes

Reaction equation

HRID 558613 reaction equation
[Br:1][C:2]1[C:3]([NH2:18])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:7]=1.C(=O)(O)[O-].[Na+].Cl[CH2:25][CH:26]=O>CCO>[Br:1][C:2]1[C:3]2[N:4]([CH:25]=[CH:26][N:18]=2)[CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 67000967HCID 67000967, compound

Product 1

HCID 67000913HCID 67000913, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of 3-bromo-5-(4-trifluoromethyl-phenyl)-pyridin-2-ylamine (example C.25 step 2) (4.96 g, 16 mmol) and sodium bicarbonate (5.256 g, 63 mmol) in EtOH (20 mL) at 50° C. was dropwise added chloroacetaldehyde (50% in water, 3.66 mL, 31 mmol) within 2 h. Cooled to 23° C. and evaporated all volatiles The residue was purified by silica gel column chromatography with dichloromethane/methanol followed by trituration with heptane and very little ether to give the title compound as a white solid (3.4 g, 63%). MS (ISP) 340.9 [(M+H)+], 343.1 [(M+2+H)+].

Workup

  1. customat 50° C.
  2. customwithin 2 h
  3. customevaporated all volatiles The residue
  4. customwas purified by silica gel column chromatography with dichloromethane/methanol

Sources & evidence

ORD record
ord-13e8e3c2d692494a8b70db36146ce3b9
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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