Ethyl Acetate → HCID 56646051, compound
Reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]2[CH:21]=[CH:20][C:19](B3OC(C)(C)C(C)(C)O3)=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:32]1[CH:37]=[CH:36][C:35]([N:38]2[C:50]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3C3C2=CC=CC=3)=[CH:34][CH:33]=1.[F-].[K+].C(O[CH2:57][CH3:58])(=O)C>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:16]2[CH:17]=[CH:18][C:19]([C:58]3[CH:57]=[CH:3][C:2]([N:38]4[C:50]5[CH:45]=[CH:46][CH:47]=[CH:48][C:49]=5[C:34]5[C:35]4=[CH:36][CH:37]=[CH:32][CH:33]=5)=[CH:1][CH:6]=3)=[CH:20][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
A mixture of Compound 10 (1.41 g, 3.56 mmol), 9-(4-bromophenyl)-9H-carbazole (1.15 g, 3.56 mmol), Pd(dppf)Cl2 (100 mg, 0.14 mmol) and KF (0.619 g, 10.7 mmol) in anhydrous DMF (20 mL) was heated at 120° C. under argon overnight. After cooling to r.t., ethyl acetate (200 mL) was added and the whole was stirred for 15 min. The resulting mixture was filtered. The solid was collected and dissolved in DCM (200 mL), which was filtered, concentrated and recrystallized to give a white solid (Compound 11) (550 mg).
Workup
- temperatureAfter cooling to r.t.
- filtrationThe resulting mixture was filtered
- customThe solid was collected
- dissolutiondissolved in DCM (200 mL)
- filtrationwhich was filtered
- concentrationconcentrated
- customrecrystallized
Sources & evidence
- ORD record
- ord-c3016609593f40bda2483f623b1c8ef4
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08771845B2
Reaction notes
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