Dichloromethane → HCID 90460781, compound

HRID 2202121Notes

Reaction equation

HRID 2202121 reaction equation
Br[C:2]1[N:3]=[CH:4][N:5]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)#[N:21].C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:20]([C:22]1[CH:27]=[CH:26][C:25]([C:2]2[N:3]=[CH:4][N:5]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:24][CH:23]=1)#[N:21]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 90460857HCID 90460857, compound

Product 1

HCID 90460781HCID 90460781, compoundYield 82.4%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 4-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazole-5-carboxylate (3.48 g, 9.96 mmol, 1.00 equiv), (4-cyanophenyl)boronic acid (3.0 g, 20.42 mmol, 2.00 equiv), Pd(dppf)Cl2.CH2Cl2 (0.42 g, 0.06 equiv) and potassium carbonate (4.0 g, 3.00 equiv) in N,N-dimethylformamide (20 mL) was stirred under nitrogen at 100° C. for 5 h. The reaction was cooled to room temperature and then diluted with 100 mL of ethyl acetate. The mixture was washed with 4×50 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified on a silica gel column eluted with 0-20% of ethyl acetate in petroleum ether to give 3.05 g (82%) of ethyl 4-(4-cyanophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-5-carboxylate as a yellow oil. LCMS (method A, ESI): RT=1.62 min, m/z=372.0 [M+H]+.

Workup

  1. washThe mixture was washed with 4×50 mL of brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column
  5. washeluted with 0-20% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-69faeec1cfea47c4b4281ee033259c40
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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