Ammonium Chloride → HCID 66778779, compound

HRID 2091029Notes

Reaction equation

HRID 2091029 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([CH:12]=[O:13])[N:11]=2)[CH:8]=1.[CH:16]1([Mg]Br)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[Cl-].[NH4+]>O1CCCC1>[CH:16]1([CH:12]([C:10]2[N:11]=[C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:8][N:7]3[CH:9]=2)[OH:13])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 716072286-(Trifluoromethyl)imidazo[1,2-a]pyridine-2-carbaldehydeHCID 178419651HCID 178419651, compound

Product 1

HCID 66778779HCID 66778779, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carbaldehyde (2.1 g) synthesized above in tetrahydrofuran (40 mL) was added dropwise cyclohexylmagnesium bromide (1M tetrahydrofuran solution, 15 mL) at 0° C. After stirring at 0° C. for 1 hr, aqueous ammonium chloride solution was added. The mixture was extracted with ethyl acetate, and the solvent was evaporated under reduced pressure. The precipitate was washed with ethanol-diisopropyl ether to give the title object compound (0.9 g, 30%) as a colorless solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customthe solvent was evaporated under reduced pressure
  3. washThe precipitate was washed with ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-4bbc383ff30149cf873d7d41b751cb98
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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