Sodium Carbonate → HCID 67548165, compound

HRID 2064487Notes

Reaction equation

HRID 2064487 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:7]=1.[NH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:17][C:18]1[CH:23]=[C:22]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[CH:7]=2)[CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 577502345-Bromo-N-(4-methoxyphenyl)pyridin-3-amine

Product 1

HCID 67548165HCID 67548165, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 3-bromo-5-(p-methoxyphenylamino)pyridine (0.5 g, 1.8 mmol), 3-aminophenyl boronic acid (0.28 g, 1.8 mmol) and Na2CO3 (0.56 g, 5.3 mmol) in dimethoxyethane (10 ml) and water (3.5 ml) is deoxygenated using argon before adding Pd(PPh3)4 (0.06 g) and heating the mixture at reflux for 16 hours. The mixture is diluted with ethyl acetate, washed with brine, dried over Na2SO4 and concentrated. The residue is chromatographed on silicagel to afford the product; 1H NMR (400 MHz, d6-DMSO): δ 8.16 (m, 2H), 8.10 (s, 1H), 7.34 (m, 1H), 7.10 (m, 3H), 6.91 (d, J=8.84 Hz, 2H), 6.75 (s, 1H), 6.71 (m, 1H), 6.57 (m, 1H), 5.21 (br s, 2H), 3.73 (s, 3H).

Workup

  1. temperatureheating the mixture
  2. temperatureat reflux for 16 hours
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silicagel
  7. customto afford the product

Sources & evidence

ORD record
ord-b34e002db5dd48d191ad2706beac0207
Source dataset
uspto-grants-2012_10
Patent number
US08288421B2

Reaction notes

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