Sodium Bicarbonate → HCID 178428705, compound

HRID 505402Notes

Reaction equation

HRID 505402 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9][CH2:10][C:11]2[NH:20][C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[N:12]=2)[N:3]=1.C(=O)(O)[O-].[Na+].[C:26]1(B2OCCCO2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCOCC1>[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9][CH2:10][C:11]2[NH:20][C:14]3=[N:15][CH:16]=[C:17]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:18]=[C:13]3[N:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 642685Phenylboronic acid 1,3-propanediol esterHCID 178428704HCID 178428704, compound2×

Product 1

HCID 178428705HCID 178428705, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

350 mg of 2-[2-(amino-4-methylpyridin-6-yl)ethyl]-6-bromo-3H-imidazo[4,5-b]pyridine (compound 4) are dissolved in 5.6 ml of anoxic dioxane under a nitrogen atmosphere. Subsequently, 3.15 ml of an aqueous sodium bicarbonate solution (2.0 M), 193 mg of 2-phenyl-1,3,2-dioxaborinane, and 49 mg of trans-dichloro-bis(tricyclohexylphosphane)palladium-(II) are added. The reaction mixture is refluxed at 110° C. for 46 hours. Thereafter, the volatile components are removed in vacuo and the remaining residue is redissolved in 200 ml of a mixture of water/dichloromethane (1:1). The aqueous phase is extracted twice each with 125 ml of dichloromethane. The organic layer is separated, dried using sodium sulfate, and evaporated to dryness to yield a colorless, crude solid. Subsequently, the residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 8:1) to afford 279 mg of the title compound as a colorless solid of m.p. 230° C. MS: 330.3 (MH+). TLC: Rf=0.34 (dichloromethane/methanol 8:1).

Workup

  1. customThereafter, the volatile components are removed in vacuo
  2. dissolutionthe remaining residue is redissolved in 200 ml of a mixture of water/dichloromethane (1:1)
  3. extractionThe aqueous phase is extracted twice each with 125 ml of dichloromethane
  4. customThe organic layer is separated
  5. customdried
  6. customevaporated to dryness
  7. customto yield a colorless, crude solid
  8. customSubsequently, the residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 8:1)

Sources & evidence

ORD record
ord-f499970186cc42e583f421d0829cf0fe
Source dataset
uspto-grants-2010_08
Patent number
US07781453B2

Reaction notes

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