Dichloromethane → HCID 66797840, compound

HRID 2275948Notes

Reaction equation

HRID 2275948 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([N:27]4[C:39]5[CH:38]=[C:37]6[C:40]([CH3:48])([CH3:47])[C:41]7[C:46]([C:36]6=[CH:35][C:34]=5[C:33]5[C:28]4=[CH:29][CH:30]=[CH:31][CH:32]=5)=[CH:45][CH:44]=[CH:43][CH:42]=7)=[CH:23][CH:22]=3)=[CH:17][CH:16]=1)[C:10]1[CH:9]=[C:8]3[C:49]([CH3:57])([CH3:56])[C:50]4[C:55]([C:7]3=[CH:6][C:5]2=1)=[CH:54][CH:53]=[CH:52][CH:51]=4.[B:58]1(B2OC(C)(C)C(C)(C)O2)[O:62][C:61]([CH3:64])([CH3:63])[C:60]([CH3:66])([CH3:65])[O:59]1.C([O-])(=O)C.[K+].ClCCl>O1CCOCC1>[CH3:65][C:60]1([CH3:66])[C:61]([CH3:64])([CH3:63])[O:62][B:58]([C:2]2[CH:3]=[C:4]3[C:12](=[CH:13][CH:14]=2)[N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[C:39]6[CH:38]=[C:37]7[C:40]([CH3:48])([CH3:47])[C:41]8[C:46]([C:36]7=[CH:35][C:34]=6[C:33]6[C:28]5=[CH:29][CH:30]=[CH:31][CH:32]=6)=[CH:45][CH:44]=[CH:43][CH:42]=8)=[CH:23][CH:22]=4)=[CH:17][CH:16]=2)[C:10]2[CH:9]=[C:8]4[C:49]([CH3:57])([CH3:56])[C:50]5[C:55]([C:7]4=[CH:6][C:5]3=2)=[CH:54][CH:53]=[CH:52][CH:51]=5)[O:59]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 66798025HCID 66798025, compound

Product 1

HCID 66797840HCID 66797840, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7.1 g (9.0 mmol) of 4-(7-bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluoren-10-yl)-4′-(12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluoren-10-yl)biphenyl, 2.5 g (9.85 mmol) of bis(pinacolato)diborane and 2.6 g (26 mmol) of potassium acetate are suspended in 500 ml of dioxane. 0.22 g (0.27 mmol) of 1,1-bis(diphenylphosphino)ferrocenepalladium(II) dichloride complex with dichloromethane is added to this suspension. The reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, washed three times with 150 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene. The yield is 6.8 g (8 mmol, 90%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. washwashed three times with 150 ml of water
  6. customsubsequently evaporated to dryness
  7. customThe residue is recrystallised from toluene

Sources & evidence

ORD record
ord-c2734812dcc3445382cb5863ce3e857c
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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