O-Xylene → HCID 57936337, compound

HRID 1434985Notes

Reaction equation

HRID 1434985 reaction equation
BrC1C=CC([N:8]([C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=CC=1.C([Sn](CCCC)(CCCC)[C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)CCC.[C:44]1(C)[C:45](C)=[CH:46][CH:47]=[CH:48][CH:49]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:33]1[CH:32]=[CH:31][C:30]([C:44]2[CH:45]=[CH:46][C:47]([C:21]3[CH:22]=[CH:23][N:24]=[C:19]([NH:8][CH:9]4[CH2:14][C:13]([CH3:15])([CH3:16])[NH:12][C:11]([CH3:17])([CH3:18])[CH2:10]4)[N:20]=3)=[CH:48][CH:49]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 27373184-(Tri-n-butylstannyl)pyridineHCID 86610958HCID 86610958, compound

Product 1

HCID 57936337HCID 57936337, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

[4-(4-Bromophenyl (pyrimidin-2-yl]-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (116 mg; 0.3 mmol), PdCl2(PPh3)2 (21 mg; 0.03 mmol) and 4-tributylstannanyl-pyridine (221 mg; 0.6 mmol) were heated in xylene (3 ml) at 100° C. for 1 hour. The reaction mixture was filtered, evaporated and purified by preparative HPLC to give the title compound as a white solid. Yield: 20 mg (17%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-5d042659c564452199c7b6691bfcbf69
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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