Potassium Carbonate → 4-(5-bromopyridin-2-yl)-N,N-di-p-tolylaniline

HRID 1755523Notes

Reaction equation

HRID 1755523 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([N:7]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.I[C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][N:27]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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>[Br:32][C:29]1[CH:30]=[CH:31][C:26]([C:11]2[CH:12]=[CH:13][C:8]([N:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:24])=[CH:6][CH:5]=3)[C:17]3[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=3)=[CH:9][CH:10]=2)=[N:27][CH:28]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5936905-Bromo-2-iodopyridineHCID 23083792[4-[Bis(4-methylphenyl)amino]phenyl]boronic acid2×

Product 1

HCID 867120514-(5-bromopyridin-2-yl)-N,N-di-p-tolylanilineYield 82%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
95 °C

Procedure

A mixture of (4-(di-p-tolylamino)phenyl)boronic acid (Compound 26) (3.17 g, 10 mmol), 2-iodo-5-bromo-pyridine (5.68 g, 20 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol) and K2CO3 (2.76 g, 20 mmol) in dioxane/water (80 mL/15 mL) was degassed and heated at about 95° C. overnight. The resulting solution was diluted with ethyl acetate (200 mL), loaded on silica gel, and purified by flash column (hexanes to hexanes/dichloromethane 9:1 to 4:1 to 3:2). The desired fraction was collected and concentrated to give a light yellow solid (Compound 27) (3.5 g, in 82% yield).

Workup

  1. customwas degassed
  2. additionThe resulting solution was diluted with ethyl acetate (200 mL)
  3. custompurified by flash column (hexanes to hexanes/dichloromethane 9:1 to 4:1 to 3:2)
  4. customThe desired fraction was collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-012974b22b8f48e6a3822a5608da3447
Source dataset
uspto-grants-2015_10
Patent number
US09172051B2

Reaction notes

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