Dimethylformamide → HCID 56943704, compound

HRID 1026763Notes

Reaction equation

HRID 1026763 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]([CH:16]([CH3:18])[CH3:17])[C:8]([C:10]2[N:11]=[CH:12][N:13]([CH3:15])[CH:14]=2)=[O:9])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.Br[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.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>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]([CH:16]([CH3:17])[CH3:18])[C:8]([C:10]2[N:11]=[CH:12][N:13]([CH3:15])[CH:14]=2)=[O:9])=[CH:4][C:3]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 86690489HCID 86690489, compound

Product 1

HCID 56943704HCID 56943704, compoundYield 28.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-[4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]-1-methyl-N-(propan-2-yl)-1H-imidazole-4-carboxamide (100 mg), 2-bromopyridine (47 mg), tetrakis(triphenylphosphine)palladium (29 mg), potassium carbonate (69 mg), dimethylformamide (1.0 mL) and ethanol (0.5 mL) was stirred under irradiation with microwave while heating at 150° C. for 50 min. After the mixture was diluted with ethyl acetate, the insoluble matter was filtered off, and the solvent was distilled off under reduced pressure. The residue was diluted with ethyl acetate, and then washed with water and brine. The organic phase was collected and dried over sodium sulfate, the desiccant was filtered off and the solvent was then distilled off under reduced pressure. The resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100) and (silica gel cartridge, chloroform:methanol=100:0-98:2) to afford the title compound (25 mg).

Workup

  1. filtrationthe insoluble matter was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water and brine
  5. customThe organic phase was collected
  6. dry with materialdried over sodium sulfate
  7. filtrationthe desiccant was filtered off
  8. distillationthe solvent was then distilled off under reduced pressure
  9. customThe resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100) and (silica gel cartridge, chloroform:methanol=100:0-98:2)

Sources & evidence

ORD record
ord-32f315e9e0eb454281c965d534a87856
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

Loading…