Methanol → Methyl 2-(4-(4-amino-2-methyl-1H-indol-5-yloxy)-2,3-dimethylphenyl)acetate

HRID 2423289Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][C:10]2[C:11]([N+:20]([O-])=O)=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([CH3:19])=[CH:13]3)[CH:5]=[CH:4][C:3]=1[CH2:23][C:24]([OH:26])=[O:25].O.O.[Sn](Cl)(Cl)(Cl)Cl.[CH3:34]O>C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[NH2:20][C:11]1[C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([CH2:23][C:24]([O:26][CH3:34])=[O:25])=[C:2]([CH3:1])[C:7]=2[CH3:8])=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([CH3:19])[NH:15]2

Participants

Conditions

Temperature: 60 °C

Procedure

Under an N2 atmosphere, 2-(2,3-dimethyl-4-(2-methyl-4-nitro-1H-indol-5-yloxy)phenyl)acetic acid (0.335 g, 0.946 mmol) was suspended in methanol and tin chloride dihydrate (1.71 g, 7.57 mmol) was added. The reaction was heated to 60° C. for 16 h. The reaction was diluted with ethyl acetate and 10% NaHCO3 (aq). The layers were separated and the organic layer was washed with water (3×), dried (Na2SO4), filtered and concentrated in vacuo. Flash column chromatography of the residue, eluting with 20% to 80% ethyl acetate in hexanes, afforded the title compound. LC-MS ESI (pos.) m/z: 339.2 (M+H).

Workup

customThe layers were separated
washthe organic layer was washed with water (3×)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
washFlash column chromatography of the residue, eluting with 20% to 80% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-b404200bf81e48bc8374df64ba8ecc2c
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960567B2

Reaction notes

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