Potassium Phosphate, Tribasic → HCID 178435922, compound

HRID 81235Notes

Reaction equation

HRID 81235 reaction equation
Br[C:2]1[N:19]([CH2:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]2)[C:5]2[C:6]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=3)=[N:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[N:3]=1.CC1(C)C(C)(C)OB([C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH2:37])O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].ClCCl>[Cl:18][C:16]1[CH:17]=[C:12]([C:6]2[C:5]3[N:19]([CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]4)[C:2]([C:36]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH2:37])=[N:3][C:4]=3[CH:9]=[C:8]([C:10]#[N:11])[N:7]=2)[CH:13]=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 110316711-Phenylvinylboronic acid, pinacol esterHCID 178461197HCID 178461197, compound

Product 1

HCID 178435922HCID 178435922, compound

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Conditions

Temperature
50 °C

Procedure

A sealed tube was charged with 2-bromo-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (Preparative Example 3.1, 150 mg, 0.337 mmol), 4,4,5,5-tetramethyl-2-(1-phenylethenyl)-1,3,2-dioxaborolane (93 mg, 0.405 mmol), PdCl2(dppf)-dichloromethane adduct (27.5 mg, 0.034 mmol), and potassium phosphate (215 mg, 1.012 mmol). The tube was evacuated and backfilled with argon (3×). Fully degassed dioxane (1.53 mL) and water (0.153 mL) were added. The vial was sealed and heated at 50° C. overnight. The mixture was then cooled to room temperature and directly purified via silica gel chromatography (0-100% ethyl acetate/hexanes) to afford 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-(1-phenylethenyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile as a yellow solid. MS ESI calcd. for C28H26ClN5 [M+H]+ 468. found 468.

Workup

  1. customThe tube was evacuated
  2. additionFully degassed dioxane (1.53 mL) and water (0.153 mL) were added
  3. customThe vial was sealed
  4. temperatureThe mixture was then cooled to room temperature
  5. customdirectly purified via silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a3a7ec8b04a94bc09bc86b1b6a7ecbef
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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