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Chloroform → HCID 86690488, compound

HRID 1026762
Notes
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Reaction equation

HRID 1026762 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][N:9]([CH:18]([CH3:20])[CH3:19])[C:10]([C:12]2[N:13]=[CH:14][N:15]([CH3:17])[CH:16]=2)=[O:11])[CH:5]=[CH:4][N:3]=1.[F:21][C:22]([F:34])([F:33])[O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.C(Cl)(Cl)[Cl:47]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[ClH:47].[ClH:47].[CH3:17][N:15]1[CH:16]=[C:12]([C:10]([N:9]([CH:18]([CH3:20])[CH3:19])[CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:27]3[CH:26]=[CH:25][C:24]([O:23][C:22]([F:21])([F:33])[F:34])=[CH:29][CH:28]=3)[CH:7]=2)=[O:11])[N:13]=[CH:14]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 6212ChloroformHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 86690468HCID 86690468, compound

Product 1

HCID 86690488HCID 86690488, compound

Reagents, catalysts & solvents

2
HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-[(2-bromopyridin-4-yl)methyl]-1-methyl-N-(propan-2-yl)-1H-imidazole-4-carboxamide (100 mg), 4-trifluoromethoxyphenylboronic acid (122 mg), tetrakis(triphenylphosphine)palladium (34 mg), potassium carbonate (82 mg), dimethylformamide (1.2 mL) and ethanol (0.4 mL) was stirred under irradiation with microwave while heating at 150° C. for 30 min. After diluting with chloroform, the mixture was washed with water and further extracted with chloroform. The organic phase was separated out, and the solvent was distilled off under reduced pressure. The resulting residue was diluted with ethyl acetate, and a small amount of NH silica gel was added thereto, followed by stirring. The NH silica gel was filtered off, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by HPLC. The resulting residue was dissolved in acetonitrile and water, and 2N hydrochloride was added thereto, followed by lyophilization to afford the title compound (94 mg).

Workup

  1. washthe mixture was washed with water
  2. extractionfurther extracted with chloroform
  3. customThe organic phase was separated out
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe resulting residue was diluted with ethyl acetate
  6. additiona small amount of NH silica gel was added
  7. stirringby stirring
  8. filtrationThe NH silica gel was filtered off
  9. distillationthe solvent was then distilled off under reduced pressure
  10. customThe resulting residue was purified by HPLC
  11. dissolutionThe resulting residue was dissolved in acetonitrile
  12. additionwater, and 2N hydrochloride was added

Sources & evidence

ORD record
ord-106f0f61b3c84038ae41050860caedac
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08729271B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes