2,6-Dimethylaniline → HCID 135979345, compound

HRID 1694530Notes

Reaction equation

HRID 1694530 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:15]=[C:14]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:13]=1[OH:26])[CH:8]=[CH:7]2.[CH3:27][C:28]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:29]=1[NH2:30].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC([O-])(C)C.[Na+]>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].O.C1(C)C=CC=CC=1>[C:22]([C:14]1[CH:15]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:17]=[C:12]([C:9]2[CH:8]=[CH:7][C:6]3[C:11](=[C:2]([NH:30][C:29]4[C:31]([CH3:35])=[CH:32][CH:33]=[CH:34][C:28]=4[CH3:27])[CH:3]=[CH:4][CH:5]=3)[N:10]=2)[C:13]=1[OH:26])([CH3:25])([CH3:24])[CH3:23]

Participants

8

Reactant 4

HCID 68962,6-DimethylanilineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 135979344HCID 135979344, compound

Product 1

HCID 135979345HCID 135979345, compound

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(8-bromo-2-quinolinyl)-4,6-di-tert-butylphenol (3.3 g, 8 mmol), 2,6-dimethylaniline (1.2 mL, 10 mmol), Pd(dba)2 (0.036 g, 0.6 mmol), L=(N-[2′-(dicyclohexylphosphino)[1,1′-biphenyl]-2-yl]-N,N-dimethylamine) (0.05 g, 0.12 mmol), NaOtBu (0.36 g, 3.6 mmol), and toluene (8 mL) is stirred for 8 h under an argon atmosphere at 100° C. The mixture is then poured into water and extracted with benzene (3×50 mL). The combined organic phase is washed with water and brine, and is then concentrated. The residue is purified by column chromatography (silica gel 40, hexane/toluene 2:1). Yield: 2.17 g (60%).

Workup

  1. extractionextracted with benzene (3×50 mL)
  2. washThe combined organic phase is washed with water and brine
  3. concentrationis then concentrated
  4. customThe residue is purified by column chromatography (silica gel 40, hexane/toluene 2:1)

Sources & evidence

ORD record
ord-f95f8a3a2c0f4b32aab5d4a598dd6ca2
Source dataset
uspto-grants-2012_04
Patent number
US08158733B2

Reaction notes

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