Methyl N-(triethylammoniosulfonyl)carbamate → Methyl 3-(4-{6-[5-(4-methoxyphenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethylphenyl)-propionate

HRID 1513286Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:37]=[CH:36][C:6]([C:7]([NH:9][NH:10][C:11]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[C:18]([C:22]4[C:27]([CH3:28])=[CH:26][C:25]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:24][C:23]=4[CH3:35])[NH:19]3)=[CH:15][CH:14]=2)=O)=[O:8])=[CH:5][CH:4]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]2[O:8][C:11]([C:13]3[CH:21]=[C:20]4[C:16]([CH:17]=[C:18]([C:22]5[C:27]([CH3:28])=[CH:26][C:25]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:24][C:23]=5[CH3:35])[NH:19]4)=[CH:15][CH:14]=3)=[N:10][N:9]=2)=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of methyl 3-(4-{6-[N′-(4-methoxybenzoyl) -hydrazinocarbonyl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-propionate (220 mg, 440 μmol) and Burgess reagent (210 mg, 880 μmol) in THF (10 mL) was heated in a microwave apparatus at 150° C. for 30 min. The solvent was removed under reduced pressure, and the residue chromatographed using a 30-70% gradient of heptane/ethyl acetate to afford the title compound.

Workup

customThe solvent was removed under reduced pressure
customthe residue chromatographed

Sources & evidence

ORD record: ord-29fa7b11ae144b628026737e1cb8d3a9
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217065B2

Reaction notes

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