Phenylboronic Acid → HCID 67151778, compound

HRID 1529517Notes

Reaction equation

HRID 1529517 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH:7]=[C:8]4[NH:23][C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:9]4=[CH:10][C:11]=3[C:12]([CH3:16])([CH3:15])[C:13]=2[CH:14]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][C:12]1([CH3:16])[C:11]2[CH:10]=[C:9]3[C:17]4[C:22]([NH:23][C:8]3=[CH:7][C:6]=2[C:5]2[CH:4]=[CH:3][C:2]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:14][C:13]1=2)=[CH:21][CH:20]=[CH:19][CH:18]=4

Participants

5

Reactant 2

HCID 66827Phenylboronic AcidHCID 67151800HCID 67151800, compound

Product 1

HCID 67151778HCID 67151778, compound

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2.47 g (8.1 mmol) of tetrakis(triphenylphosphino)palladium(0) are added to a vigorously stirred suspension of 14.49 g (40 mmol) of 2-bromo-12,12-dimethyl-6,12-dihydro-6-azaindeno[1,2-b]fluorene, 3.69 g (40 mmol) of phenylboronic acid and 63.9 g (127 mmol) of Na2 CO3 in 500 ml of DMF, and the mixture is subsequently heated under reflux for 16 h. After cooling, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol and recrystallised three times from DMF (about 15 ml/g). Yield: 13 g (36 mmol, 91%).

Workup

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol
  6. customrecrystallised three times from DMF (about 15 ml/g)

Sources & evidence

ORD record
ord-e410d10212e840538581ec8b6bdb64c2
Source dataset
uspto-grants-2015_07
Patent number
US09090590B2

Reaction notes

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