Triethylamine → HCID 21886474, compound

HRID 723101Notes

Reaction equation

HRID 723101 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[NH2:10].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.CCN(CC)CC.[CH3:43][C:44]1([CH3:51])[C:48]([CH3:50])([CH3:49])[O:47][BH:46][O:45]1>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[Cl:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([B:46]2[O:47][C:48]([CH3:50])([CH3:49])[C:44]([CH3:51])([CH3:43])[O:45]2)=[C:3]([NH2:10])[CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 21886382Benzenamine, 2-bromo-5-chloro-3-methyl-

Product 1

HCID 21886474HCID 21886474, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-5-chloro-3-methyl-phenylamine (595 mg, 2.7 mmol, Example 135: step c), Pd(OAc)2 (30.3 mg, 0.14 mmol), 2-(dicyclohexylphosphino)biphenyl (189.2 mg, 0.54 mmol) and Et3N (1.5 mL, 10.8 mmol) were dissolved into dioxane (10 mL). To this was added 4,4,5,5-Tetramethyl-[1,3,2]dioxaborolane (1.2 mL, 8.1 mmol) slowly. The reaction was heated to 80° C. overnight. The solvents were removed in vacuo and the resulting residue was dissolved into EtOAc and washed with brine. The combined organic layers were dried (MgSO4) and removal of the solvents in vacuo resulted in a mixture of the title compound and 3-Methyl-2,5-bis-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine were obtained and used with out further purification.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe resulting residue was dissolved into EtOAc
  3. washwashed with brine
  4. customThe combined organic layers were dried
  5. custom(MgSO4) and removal of the solvents in vacuo

Sources & evidence

ORD record
ord-279f37468f6943bf97477eaa7b3aaabe
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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