Nitrogen → HCID 58251292, compound

HRID 2170452Notes

Reaction equation

HRID 2170452 reaction equation
Cl[C:2]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([C:18]2[C:31]3[C:32]4=[C:33]5[C:28](=[CH:29][CH:30]=3)[CH:27]=[CH:26][CH:25]=[C:24]5[CH:23]=[CH:22][C:21]4=[CH:20][CH:19]=2)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:34]1(B(O)O)[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1.C([O-])([O-])=O.[Cs+].[Cs+].N#N.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>O1CCOCC1.C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].CCO.O>[C:34]1([C:2]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([C:18]3[C:31]4[C:32]5=[C:33]6[C:28](=[CH:29][CH:30]=4)[CH:27]=[CH:26][CH:25]=[C:24]6[CH:23]=[CH:22][C:21]5=[CH:20][CH:19]=3)=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1

Participants

11

Reactant 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2545321-Naphthaleneboronic acidHCID 58251291HCID 58251291, compound

Product 1

HCID 58251292HCID 58251292, compound

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

43.5 g (90 mmol) of diethyl 2-chloro-5-pyren-1-ylterephthalate, 21.5 g (120 mmol) of 1-naphthylboronic acid and 58.1 g of Cs2CO3 are initially introduced in 230 ml of dry dioxane, and the mixture is saturated with N2 for 30 min. 2.7 ml of a 1.0 M solution of tri-tert-butylphosphine in toluene, followed by 300 mg (1.3 mmol) of Pd(OAc)2, are then added. The mixture is heated at the boil for 4 h and extended with water and EtOH, and the precipitate is filtered off with suction, washed with water and EtOH and dried. The solid is recrystallised three times from dioxane and then has a purity of >99% according to 1H-NMR. The yield is 44.2 g (90%) of colourless solid.

Workup

  1. additionare then added
  2. temperatureThe mixture is heated at the boil for 4 h
  3. filtrationthe precipitate is filtered off with suction
  4. washwashed with water and EtOH
  5. customdried
  6. customThe solid is recrystallised three times from dioxane

Sources & evidence

ORD record
ord-085c4377077c48c1a2b5bdd16a225f72
Source dataset
uspto-grants-2015_06
Patent number
US09051233B2

Reaction notes

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