Nitrogen → HCID 58261502, compound

HRID 2170454Notes

Reaction equation

HRID 2170454 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:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:28]1[C:42]2=[C:43]3[C:35]([C:36]4[C:41]2=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:34][CH:33]=[CH:32][C:31]3=[C:30](B(O)O)[CH:29]=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>[CH:28]1[C:42]2=[C:43]3[C:35]([C:36]4[C:41]2=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:34][CH:33]=[CH:32][C:31]3=[C:30]([C:2]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:29]=1

Participants

11

Reactant 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23088535Fluoranthen-3-ylboronic acidHCID 58261495HCID 58261495, compound

Product 1

HCID 58261502HCID 58261502, compound

Reagents, catalysts & solvents 5

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

Procedure

15.4 g (40 mmol) of diethyl 2-chloro-5-naphthalen-1-ylterephthalate, 14.0 g (56 mmol) of fluoranthene-3-boronic acid and 17.7 g of Cs2CO3 are initially introduced in 70 ml of dry dioxane and saturated with N2 for 30 min. 0.8 ml of a 1.0 M solution of tri-tert-butylphosphine in toluene, followed by 91 mg (0.4 mmol) of Pd(OAc)2 are then added. The mixture is heated at the boil for 4 h, extended with water and EtOH, the precipitate is filtered off with suction, washed with heptane and dried. The solid is recrystallised from toluene and then has, according to 1H-NMR, a purity of >95%. The yield is 8.5 g (38%) 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 heptane
  5. customdried
  6. customThe solid is recrystallised from toluene

Sources & evidence

ORD record
ord-8a5f3191c8874fda8687ed65e553ef54
Source dataset
uspto-grants-2015_06
Patent number
US09051233B2

Reaction notes

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