Sodium Carbonate → HCID 90407040, compound

HRID 2277440Notes

Reaction equation

HRID 2277440 reaction equation
Br[C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][N:9]=1.[OH:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][C:22]=1[CH3:23].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]>[OH:16][C:17]1[CH:18]=[C:19]([C:2]2[N:6]([CH3:7])[CH:5]=[N:4][C:3]=2[C:8]2[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][N:9]=2)[CH:20]=[CH:21][C:22]=1[CH3:23]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 4187664(3-Hydroxy-4-methylphenyl)boronic acidHCID 904081442-(5-Bromo-1-methylimidazol-4-yl)pyridine-4-carbonitrile

Product 1

HCID 90407040HCID 90407040, compoundYield 69%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

To a microwave vessel was added 2-(5-bromo-1-methyl-1H-imidazol-4-yl)pyridine-4-carbonitrile (79 mg, 0.3 mmol), 3-hydroxy-4-methylphenyl boronic acid (55 mg, 0.36 mmol), PdCl2(dppf) (22 mg, 0.03 mmol), 2M Na2CO3 (0.3 mL, 0.6 mmol) in 2 mL dioxane. The reaction mixture was heated in a microwave oven at 120° C. for 1 hr. It was then purified by ISCO flash column (MeOH/DCM=0-5%) to give 60 mg product (69%). 1H NMR (400 MHz, DMSO-d6): δ 2.11 (3H, s), 3.46 (3H, s), 6.71 (1H, d, J=7.6 Hz), 6.75 (1H, s), 7.12 (1H, d, J=7.7 Hz), 7.52 (1H, d, J=4.9 Hz), 7.85 (1H, s), 8.06 (1H, s), 8.50 (1H, d, J=5 Hz), 9.36 (1H, s). [M+H] Calc'd for C17H14N4O, 291. Found, 291.

Workup

  1. customIt was then purified by ISCO flash column (MeOH/DCM=0-5%)

Sources & evidence

ORD record
ord-33777049666444eb9ade7f6bf376ac7c
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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