Potassium Carbonate → 9-[3-(2,6-Diphenylpyrimidin-4-yl)phenyl]benz[4,5]-imidazo[2,1-a]isoquinoline

HRID 519423Notes

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.CC1(C)C(C)(C)OB([C:34]2[CH:50]=[CH:49][C:37]3[N:38]=[C:39]4[C:48]5[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=5[CH:42]=[CH:41][N:40]4[C:36]=3[CH:35]=2)O1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:4]1([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([C:34]4[CH:50]=[CH:49][C:37]5[N:38]=[C:39]6[C:48]7[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=7[CH:42]=[CH:41][N:40]6[C:36]=5[CH:35]=4)[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]=[CH:2][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

16 g (43.3 mmol) of 2-(3-bromophenyl)-4,6-diphenylpyrimidine and 16.5 g (48 mmol) of 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benz[4,5]-imidazo[2,1-a]isoquinoline 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 at 80° C. for 48 h under 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). Ther purity is 99.9%. Yield: 19.6 g (37 mmol) 77% of theory.

Workup

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

Sources & evidence

ORD record: ord-ee5aaafa45a44cb79d2ee50b5a832cb7
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09118022B2

Reaction notes

Loading…