Sodium Carbonate → HCID 58548616, compound

HRID 1846776Notes

Reaction equation

HRID 1846776 reaction equation
Br[C:2]1[C:3]([O:8][CH:9]2[CH2:14][CH2:13][CH:12]([C:15]3[NH:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[N:16]=3)[CH2:11][CH2:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:32]2[CH2:33][CH2:34][O:35][CH2:36][CH:37]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>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].O>[O:35]1[CH2:34][CH:33]=[C:32]([C:2]2[C:3]([O:8][CH:9]3[CH2:10][CH2:11][CH:12]([C:15]4[NH:19][C:18]5[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=5[N:16]=4)[CH2:13][CH2:14]3)=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:37][CH2:36]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 58548585HCID 58548585, compound

Product 1

HCID 58548616HCID 58548616, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

The mixture of 2-[4-(3-bromo-pyridin-2-yloxy)-cyclohexyl]-1H-benzoimidazole (0.15 g, 0.40 mmol), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (0.09, 0.40 mmol), Pd(dppf)Cl2, Na2CO3, dioxane and H2O was heated at 90° C. for 10 h under N2 atmosphere. Then the mixture was concentrated and the obtained residue was purified by silica gel chromatography (DCM:MeOH=10:1) to give 2-{4-[3-(3,6-dihydro-2H-pyran-4-yl)-pyridin-2-yloxy]-cyclohexyl}-1H-benzoimidazole (0.10 g, 0.267 mmol, 75% yield) as light yellow oil.

Workup

  1. concentrationThen the mixture was concentrated
  2. customthe obtained residue was purified by silica gel chromatography (DCM:MeOH=10:1)

Sources & evidence

ORD record
ord-a2d34b103d904c259d3adcc6bc1a3b51
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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