Dimethylformamide → HCID 58049414, compound

HRID 467964Notes

Reaction equation

HRID 467964 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[F:24])[CH2:5][N:6]([CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[C:7]([C:9]1[N:10]=[CH:11][N:12]([CH3:14])[CH:13]=1)=[O:8].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=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.O.C(O)C>[F:24][C:23]1[C:2]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:3][C:4]([CH2:5][N:6]([CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:7]([C:9]2[N:10]=[CH:11][N:12]([CH3:14])[CH:13]=2)=[O:8])=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 58049418HCID 58049418, compound

Product 1

HCID 58049414HCID 58049414, compoundYield 33.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-(3-bromo-4-fluorobenzyl)-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-1H-imidazole-4-carboxamide (150 mg), phenylboronic acid (92 mg), tetrakis(triphenylphosphine)palladium (50 mg), potassium carbonate (110 mg), DMF (2 mL) and ethanol (1 mL) was subjected to reaction in a microwave reactor (150° C., 10 min). Water was added to the reaction mixture, followed by extraction with ethyl acetate and concentrating under reduced pressure. The resulting residue was purified by TLC (silica gel) (chloroform:methanol=10:1) to give the titled compound (50 mg).

Workup

  1. customwas subjected to reaction in a microwave reactor (150° C., 10 min)
  2. extractionfollowed by extraction with ethyl acetate
  3. concentrationconcentrating under reduced pressure
  4. customThe resulting residue was purified by TLC (silica gel) (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-d001200b4e2843649ff6e34b0f6711a2
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Reaction notes

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