N-Methyloxindole → HCID 178481538, compound

HRID 24794Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C:15]1=[O:23].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[C:24]([OH:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:15]1=[O:23]

Participants

Conditions

Temperature: -70 °C

Procedure

4.15 g (41 mmol) of diisopropylamine are placed in 50 ml of THF, cooled to −70° C. and combined with a solution of 14.4 ml of (36 mmol) of n-butyl lithium solution (2.5 mol in toluene) and stirred for 10 minutes. Then a solution of 5.0 g (34 mmol) of 1-methyl-2-indolinone in 30 ml of THF is added dropwise and stirred for 45 minutes at −70° C. Then 5.8 g (0.041 mol) of benzoylchloride are added dropwise. The reaction solution is left to heat up slowly within 14 hours. It is then poured onto sodium chloride solution and extracted with ethyl acetate. The combined organic extracts are dried and concentrated by evaporation. The residue is chromatographed on silica gel (dichloromethane/methanol/ammonia=200:8:1).

Workup

stirringstirred for 45 minutes at −70° C
waitThe reaction solution is left
temperatureto heat up slowly within 14 hours
additionIt is then poured onto sodium chloride solution
extractionextracted with ethyl acetate
customThe combined organic extracts are dried
concentrationconcentrated by evaporation
customThe residue is chromatographed on silica gel (dichloromethane/methanol/ammonia=200:8:1)

Sources & evidence

ORD record: ord-a1c7c69415544c0fba466205d97cb0f2
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855710B2

Reaction notes

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