Sodium Carbonate → HCID 90407681, compound

HRID 2277546Notes

Reaction equation

HRID 2277546 reaction equation
Br[C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[CH:5]=[N:4][C:3]=1[C:16]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][N:17]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=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:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][N:6]1[C:2]([C:28]2[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=2)=[C:3]([C:16]2[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][N:17]=2)[N:4]=[CH:5]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 90407382HCID 90407382, compound

Product 1

HCID 90407681HCID 90407681, compoundYield 48%

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-(2-chlorophenyl)ethyl]imidazol-4-yl]pyridine-4-carbonitrile (1 eq), 4-fluorophenylboronic acid, Pd(dppf)Cl2 (0.1 eq) and Na2CO3 (2 eq, 2 M) in dioxane was refluxed overnight under N2. The reaction mixture was concentrated and purified by FCC (DCM/MeOH=20/1) to give the title compound (48%). [M+H] Calc'd for C23H16ClFN4, 403. Found, 403.

Workup

  1. temperaturewas refluxed overnight under N2
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by FCC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-f2af0b738cd5421eb2946fccde0c3186
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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