Toluene → HCID 66797983, compound

HRID 2275956Notes

Reaction equation

HRID 2275956 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH3:23])([CH3:22])[C:11]=2[CH:10]=1.CC(C)([O-])C.[Na+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl.O1CCOCC1>[CH3:22][C:12]1([CH3:23])[C:11]2[CH:10]=[C:9]3[NH:8][C:7]4[C:6]([C:21]3=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:5][N:4]=[CH:3][CH:2]=4

Participants

9

Reactant 5

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 66797687HCID 66797687, compound

Product 1

HCID 66797983HCID 66797983, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

500 ml of dioxane are added to 42 g of (3-chloropyridin-4-yl)-(9,9-dimethyl-9H-fluoren-2-yl)amine (130 mmol), 1.46 g of palladium(II)acetate (6.5 mmol) and 75 g of sodium tert-butoxide (780 mmol), 7.8 ml of a 1 M solution of P(t-Bu)3 in toluene (7.8 mmol), and the mixture is stirred at 105° C. under nitrogen for 24 h. 200 ml of dichloromethane and 0.1 M Na2CO3 solution are then added. The mixture is partitioned between water and dichloromethane, the aqueous phase is extracted three times with dichloromethane, the combined organic phases are dried over Na2SO4 and evaporated in a rotary evaporator. The residue is recrystallised from toluene/heptane. The yield is 18.5 g (65.1 mmol, 50%).

Workup

  1. customThe mixture is partitioned between water and dichloromethane
  2. extractionthe aqueous phase is extracted three times with dichloromethane
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. customevaporated in a rotary evaporator
  5. customThe residue is recrystallised from toluene/heptane

Sources & evidence

ORD record
ord-26f4d1ad049a4a599cb2eaa2185a95e6
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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