Oxazole → HCID 59178877, compound
Reaction equation
[Mg+2].[Br-].[Br-].[Li]CCCC.[O:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.I[C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][CH:24]([CH:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]3)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1>C1COCC1.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:36]([O:35][C:33]([N:30]1[CH2:31][CH2:32][CH:27]([CH:24]2[CH2:23][CH2:22][N:21]([C:18]3[CH:19]=[CH:20][C:15]([C:10]4[O:9][CH:13]=[CH:12][N:11]=4)=[CH:16][CH:17]=3)[CH2:26][CH2:25]2)[CH2:28][CH2:29]1)=[O:34])([CH3:39])([CH3:37])[CH3:38]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -10 °C
Procedure
A −10° C. solution of MgBr2 (37 mg; 0.202 mmol) in THF (1 mL) was treated with nBuLi (0.333 mL; 1.82M; 0.606 mmol) The solution was stirred at −10° C. for 1 hr. A solution of oxazole (42 mg; 0.606 mmol) in THF (0.5 mL) was added and the solution was stirred at 25° C. for 2 hr. This solution was added to a refluxing solution of tert-butyl 1′-(4-iodophenyl)-4,4′-bipiperidine-1-carboxylate (285 mg; 0.606 mmol) and PdCl2(dppf) (495 mg; 0.606 mmol) in THF (4 mL). The mixture was refluxed 1 hr. The reaction was partitioned between CH2Cl2 and water. The organic was dried over magnesium sulfate, filtered and evaporated to a solid. The solid was chromatographed (PTLC; 40:1 CH2Cl2/MeOH) to afford the title compound.
Workup
- stirringthe solution was stirred at 25° C. for 2 hr
- temperatureThe mixture was refluxed 1 hr
- customThe reaction was partitioned between CH2Cl2 and water
- dry with materialThe organic was dried over magnesium sulfate
- filtrationfiltered
- customevaporated to a solid
- customThe solid was chromatographed (PTLC; 40:1 CH2Cl2/MeOH)
Sources & evidence
- ORD record
- ord-7169cbd60e4343988a1459e3da388448
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445499B2
Reaction notes
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