1-Bromo-3-chlorobenzene → HCID 59264586, compound
Reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:8])[CH:5]=[CH:6][CH:7]=1.[N:9]1([C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(O[Na])(C)(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:18]([O:17][C:15]([N:9]1[CH2:14][CH2:13][N:12]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[CH:3]=2)[CH2:11][CH2:10]1)=[O:16])[CH:19]([CH3:21])[CH3:20]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 140 °C
Procedure
3-bromo chlorobenzene (434 mg, 2.3 mmol), isobutyl piperazine-1-carboxylate 6 (324 mg, 1.7 mmol), Pd2(dba)3 (32 mg, 0.035 mmol), t-BuONa (251 mg, 2.6 mmol), and Xantphos (60 mg, 0.11 mmol) in dry toluene (5 mL) were sealed in a microwave vessel and heated by microwave irradiation at 140° C. for 40 seconds. The reaction mixture was cooled and diluted with 10 mL of CH2Cl2, washed with water (5 mL), dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)); LC/MS: m/z 297.4 (M+H)+, r.t: 3.84 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), to give 13.
Workup
- temperatureThe reaction mixture was cooled
- washwashed with water (5 mL)
- dry with materialdried over Na2SO4
- customevaporated under reduced pressure
- customThe residue was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))
Sources & evidence
- ORD record
- ord-e13ba9e2ad1b4c169acd15298a539a5e
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07705002B2
Reaction notes
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