3,4-Dichloroaniline → HCID 10226296, compound

HRID 2375478Notes

Reaction equation

HRID 2375478 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[N:25]=[C:24]([N:26]([CH3:28])[CH3:27])[CH:23]=[C:22](Cl)[N:21]=2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:30][C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][C:37]=1[Cl:38])[NH2:34].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[N:21]=[C:22]([NH:34][C:33]3[CH:35]=[CH:36][C:37]([Cl:38])=[C:31]([Cl:30])[CH:32]=3)[CH:23]=[C:24]([N:26]([CH3:28])[CH3:27])[N:25]=2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 72573,4-DichloroanilineHCID 634876Binap, (A+-)-HCID 21101361HCID 21101361, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10226296HCID 10226296, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Potassium tert-butoxide (1.6 mmol, 1 M in 2-methyl 2-propanol) was added to a solution of N-[2-(4-benzyl-1-piperazinyl)-6-chloro-4-pyrimidinyl]-N,N-dimethylamine (0.331 g, 0.997 mmol) and 3,4 dichloroaniline (0.178 g, 1.10 mmol) in dioxane (2 mL). Subsequently, tris(dibenzylidineacetone)dipalladium (40 mg, 0.04 mmol) and 2,2′-Bis(diphenylphosphino)-1,1′-binapthyl (44 mg, 0.070 mmol) were added and the mixture was stirred for 7 h at 110° C. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The residue was treated with saturated NaHCO3 (50 mL) and extracted with CH2Cl2 (3×50 mL). The organic layer washed with brine (2×100 mL), dried over Na2SO4, concentrated in vacuo, and purified by preparative TLC using hexane/EtOAc to give the desired product (300 mg, 65%).

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was treated with saturated NaHCO3 (50 mL)
  4. extractionextracted with CH2Cl2 (3×50 mL)
  5. washThe organic layer washed with brine (2×100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by preparative TLC

Sources & evidence

ORD record
ord-0e17b5d5d1094a428ba5460323ec4ffd
Source dataset
uspto-grants-2008_12
Patent number
US07465750B2

Reaction notes

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