Potassium Carbonate → HCID 86691485, compound

HRID 576493Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:21]3[CH:20]=[CH:19][C:18]4[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=4[C:16]=3[N:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]2[CH:29]=[CH:28][CH:27]=[CH:26][C:13]=23)=[CH:4][CH:3]=1.C1([N:36]2[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=3[N:38]=[C:37]2[C:45]2[CH:50]=[CH:49][C:48](B3OC(C)(C)C(C)(C)O3)=[CH:47][CH:46]=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:2]1([N:36]2[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=3[N:38]=[C:37]2[C:45]2[CH:46]=[CH:47][C:48]([C:2]3[CH:7]=[CH:6][C:5]([C:8]4[C:21]5[CH:20]=[CH:19][C:18]6[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=6[C:16]=5[N:15]=[C:14]5[C:9]=4[CH:10]=[CH:11][C:12]4[CH:29]=[CH:28][CH:27]=[CH:26][C:13]=45)=[CH:4][CH:3]=3)=[CH:49][CH:50]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

6 (2.1 g, 4.8 mmol), 1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole (3.8 g, 9.6 mmol), Palladium tetrakis triphenylphoshine (830 mg) and 17 mL of a 1M potassium carbonate solution in water were introduced in a flask together with 35 mL degassed toluene. This mixture is stirred at 80° C. during 36 hours before being let cooled to room temperature and filtered. The solid is then dissolved in dichloromethane (600 mL) and filter over a Celite pad. The volatiles are removed by rotary evaporation and the solid is then dried overnight in a vacuum oven.

Workup

customdegassed toluene
temperaturebefore being let cooled to room temperature
filtrationfiltered
dissolutionThe solid is then dissolved in dichloromethane (600 mL)
filtrationfilter over a Celite pad
customThe volatiles are removed by rotary evaporation
customthe solid is then dried overnight in a vacuum oven

Sources & evidence

ORD record: ord-8596e0a1e534424895b674e10d422143
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040175B2

Reaction notes

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