Potassium Carbonate → 7-[3-(4,6-Diphenylpyrimidin-2-yl)phenyl]-12,12-dimethyl-10-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 634552Notes

Reaction equation

HRID 634552 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.B([C:29]1[CH:30]=[C:31]2[C:39](=[CH:40][CH:41]=1)[N:38]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:37]1[CH:36]=[C:35]3[C:48]([CH3:56])([CH3:55])[C:49]4[C:54]([C:34]3=[CH:33][C:32]2=1)=[CH:53][CH:52]=[CH:51][CH:50]=4)(O)O.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:20]1([C:10]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=[C:8]([C:4]3[CH:3]=[C:2]([C:29]4[CH:30]=[C:31]5[C:39](=[CH:40][CH:41]=4)[N:38]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[C:37]4[CH:36]=[C:35]6[C:48]([CH3:56])([CH3:55])[C:49]7[C:54]([C:34]6=[CH:33][C:32]5=4)=[CH:53][CH:52]=[CH:51][CH:50]=7)[CH:7]=[CH:6][CH:5]=3)[N:9]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 589431812-(3-Bromophenyl)-4,6-diphenylpyrimidineHCID 866960867-Borono12,12-dimethyl-10-phenyl-10,12-dihydro-10-aza-indeno[2,1-b]fluorene

Product 1

HCID 866960877-[3-(4,6-Diphenylpyrimidin-2-yl)phenyl]-12,12-dimethyl-10-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

16 g (43.3 mmol) of 2-(3-bromophenyl)-4,6-diphenylpyrimidine 14 and 19.3 g (48 mmol) of 7-borono12,12-dimethyl-10-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene 13 are dissolved in 80 ml of toluene and degassed. 281 ml of a degassed 2M K2CO3 and 2.5 g (2.2 mmol) of Pd(OAc)2 are added. The reaction mixture is subsequently stirred for 48 h at 80° C. under a protective-gas atmosphere. Additional toluene is added to the cooled solution, which is washed a number of times with water, dried and evaporated. The product is purified by column chromatography on silica gel with toluene/heptane (1:2). The purity is 99.9%. Yield: 22 g (31 mmol), 77% of theory.

Workup

  1. customdegassed
  2. washis washed a number of times with water
  3. customdried
  4. customevaporated
  5. customThe product is purified by column chromatography on silica gel with toluene/heptane (1:2)

Sources & evidence

ORD record
ord-8c632538039846adae8d95f356cb842c
Source dataset
uspto-grants-2016_04
Patent number
US09324954B2

Reaction notes

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