Tributylamine → 1-(1,1-Dimethylethyl) 5-methyl 2,3-dihydro-1H-indole-1,5-dicarboxylate

HRID 1944542Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CCCC)CCCC)CCC.[C]=O>CO.C1(P([Pd-](Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:5][C:6]([C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)=[O:7]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 5-bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (4.0 g, 13.5 mmol), tributylamine and bis-triphenylphosphinopalladium(II) chloride (0.65 g, 0.926 mmol) in methanol was sealed in a Parr pressure apparatus and pressurized with 600 psi of carbon monoxide. The solution was heated at 100° C. for one week. The vessel was cooled to room temperature and the gas vented. The solution was filtered, and the solvent was evaporated in vacuo. The residue was purified by flash chromatography, on silica gel eluted with 10-40% ethyl acetate in hexane to give the product mixed with tributylamine, 2.5 g (67%). The product was used without further purification in the subsequent step.

Workup

temperatureThe vessel was cooled to room temperature
filtrationThe solution was filtered
customthe solvent was evaporated in vacuo
customThe residue was purified by flash chromatography, on silica gel
washeluted with 10-40% ethyl acetate in hexane
customto give the product
customThe product was used without further purification in the subsequent step

Sources & evidence

ORD record: ord-ca2a02af4bdd478aaacee58e36d270a7
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394828B2

Reaction notes

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