Bromobenzene → HCID 86669532, compound

HRID 1468590Notes

Reaction equation

HRID 1468590 reaction equation
[CH3:1][O:2][C:3]1[C:4](N)=[N:5][CH:6]=[CH:7][CH:8]=1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC(C)([O-])C.[Na+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH2:4][N:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 99203842-Amino-3-methoxypyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 86669532HCID 86669532, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A 1 L 3-neck flask is charged with 3-methoxypyridine-2-amine (17.65 g, 143 mmol), bromobenzene (15 g, 96 mmol), Pd2DBA3 (1.75 g, 1.91 mmol), Sodium tert-butoxide (18.36 g, 101 mmol), S-Phos (1.56 g, 3.82 mmole) and 400 mL of xylene. The reaction mixture is refluxed for 4 h. The product is isolated by column chromatography (5% EtoAc in Hexs) to yield the desired product.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 h
  2. customThe product is isolated by column chromatography (5% EtoAc in Hexs)

Sources & evidence

ORD record
ord-6cc89e890f624605a0f3539a143943e8
Source dataset
uspto-grants-2015_04
Patent number
US09005772B2

Reaction notes

Loading…