Sodium Carbonate → 3-(4-Butoxyphenyl)pyridin-2-amine

HRID 1748092Notes

Reaction equation

HRID 1748092 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)[CH2:8][CH2:9][CH3:10].Br[C:22]1[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=1>COCCOC.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>[CH2:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:22]2[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:14][CH:13]=1)[CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 8177002-Amino-3-bromopyridineHCID 38363104-Butoxyphenylboronic Acid

Product 1

HCID 667483793-(4-Butoxyphenyl)pyridin-2-amineYield 61.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of sodium carbonate (0.978 g), tetrakis(triphenylphosphine)palladium(0) (0.267 g), 4-butoxyphenylboronic acid (1.16 g) and 3-bromopyridin-2-amine (0.799 g,) in DME (23 mL) and water (4.6 ml) was stirred at 80° C. overnight. The mixture was added with silica gel, concentrated in vacuo, and purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (0.690 g) as a pale yellow solid.

Workup

  1. additionThe mixture was added with silica gel
  2. concentrationconcentrated in vacuo
  3. custompurified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-fb1e809be2be40f2b0f551401d0aa781
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

Loading…