Methyl 3-iodo-4-(3-methyl-but-2-enylamino)-benzoate → Methyl 3-(propan-2-yl)-1H-indole-5-carboxylate

HRID 380440Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[C:5]([O:7][CH3:8])=[O:6]>C(N(CC)CC)C.C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:15]([C:14]1[C:10]2[C:11](=[CH:2][CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=2)[NH:12][CH:13]=1)([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of methyl 3-iodo-4-(3-methyl-but-2-enylamino)-benzoate (2.0 g, Reference Example 53) in triethylamine (1.6 ml) and acetonitrile (35 ml) was treated with palladium acetate (0.05 g). The mixture was sealed in a bomb and heated at 110° C. for 18 hours. After cooling the reaction mixture was filtered and the filtrate was evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petroleum ether (1:4, v/v) to give the title compound (1.0 g).

Workup

customThe mixture was sealed in a bomb
temperatureAfter cooling the reaction mixture
filtrationwas filtered
customthe filtrate was evaporated
additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petroleum ether (1:4, v/v)

Sources & evidence

ORD record: ord-74d097386dd44c39b63c3883741f2ca2
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303600B1

Reaction notes

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