Sodium Carbonate → HCID 90407393, compound

HRID 2277549Notes

Reaction equation

HRID 2277549 reaction equation
Br[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH:5]=[N:4][C:3]=1[C:15]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][N:16]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.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]>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][N:6]1[C:2]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)=[C:3]([C:15]2[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][N:16]=2)[N:4]=[CH:5]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 90407150HCID 90407150, compound

Product 1

HCID 90407393HCID 90407393, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-[5-bromo-1-[(2-chlorophenyl)methyl]imidazol-4-yl]pyridine-4-carbonitrile (270 mg, 0.726 mmol), 4-fluorophenylboronic acid (203 mg, 1.452 mmol), Pd(dppf)Cl2 (60 mg, 0.0726 mmol) and Na2CO3 (0.3 mL, 1.452 mmol, 2 M) in dioxane (10 mL) was refluxed overnight under N2, concentrated and purified by FCC (DCM/MeOH=20/1) to give the title compound (250 mg, 88%). [M+H] Calc'd for C22H14ClFN4, 389. Found, 389.

Workup

  1. temperaturewas refluxed overnight under N2
  2. concentrationconcentrated
  3. custompurified by FCC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-4d363536be87434fad9c99b2afe7667a
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

Loading…