Acetonitrile → tert-butyl 4-(4-(4-(ethoxycarbonyl)-2-(1H-indol-4-yl)oxazol-5-yl)phenyl)piperazine-1-carboxylate

HRID 714964Notes

Reaction equation

I[C:2]1[O:3][C:4]([C:12]2[CH:17]=[CH:16][C:15](OC)=[CH:14][CH:13]=2)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[NH:20]1[C:28]2[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[C:23]=2[CH:22]=[CH:21]1.[C:32](=[O:35])([O-])[O-:33].[Na+].[Na+].[C:38](#[N:40])[CH3:39]>C(Cl)Cl.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]>[CH2:10]([O:9][C:7]([C:5]1[N:6]=[C:2]([C:24]2[CH:25]=[CH:26][CH:27]=[C:28]3[C:23]=2[CH:22]=[CH:21][NH:20]3)[O:3][C:4]=1[C:12]1[CH:13]=[CH:14][C:15]([N:40]2[CH2:7][CH2:5][N:6]([C:32]([O:33][C:12]([CH3:17])([CH3:13])[CH3:4])=[O:35])[CH2:39][CH2:38]2)=[CH:16][CH:17]=1)=[O:8])[CH3:11]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of ethyl 2-iodo-5-(4-methoxyphenyl)oxazole-4-carboxylate (0.080 g, 0.15 mmol), indole-4-boronic acid (0.048 g, 0.30 mmol), Pd(dppf)2Cl2 (0.006 g, 0.007 mmol) and 1M aq. sodium carbonate (0.31 ml, 0.31 mmol) in acetonitrile (2.5 ml) was heated in the microwave at 150° C. for 15 minutes. The reaction mixture was diluted with DCM and washed with 1M NaOH. The organic phase was passed through a MP-SH cartridge, dried over MgSO4 and the solvent removed in vacuo to afford tert-butyl 4-(4-(4-(ethoxycarbonyl)-2-(1H-indol-4-yl)oxazol-5-yl)phenyl)piperazine-1-carboxylate which was used without further purification. LCMS (1) Rt: 2.61 min; m/z (ES+) 517.

Workup

washwashed with 1M NaOH
dry with materialdried over MgSO4
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-9ffedc196f8e4a93a1783c64a2435e95
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187465B2

Reaction notes

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