N,N'-Dimethylethylenediamine → HCID 58305308, compound

HRID 1805353Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH:21]([CH3:23])[CH3:22])[C@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=4)[NH:12][C:11]3=[O:20])[CH2:9]2)=[CH:4][CH:3]=1.[CH3:24][O:25][C:26](=[O:35])[C:27]1[CH:32]=[C:31](I)[CH:30]=[C:29]([Br:34])[CH:28]=1.C([O-])([O-])=O.[K+].[K+].CNCCNC>C(#N)C.[Cu]I>[CH3:24][O:25][C:26](=[O:35])[C:27]1[CH:32]=[C:31]([N:12]2[C:13]3[C:18](=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C@:10]3([CH2:9][C@:8]3([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH:21]([CH3:23])[CH3:22])[C:11]2=[O:20])[CH:30]=[C:29]([Br:34])[CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(1R,2R) and (1S,2S)-2-(4-chlorophenyl)-5′-fluoro-2-isopropylspiro[cyclopropane-1,3′-indolin]-2′-one prepared according to Scheme 2 (0.33 g, 1 mmol), and the 3-bromo-5-iodo-benzoic acid methyl ester (0.409 g, 1.2 mmol), CuI (20 mg), K2CO3 (0.276 g, 2 mmol) were placed in a Schlenk tube under argon atmosphere and dissolved in dry acetonitrile. The N,N′-dimethyl-1,2-ethanediamine (21 μL) was added into the mixture. The mixture was stirred at 80° C. for 14 hours. The solvent was removed in vacuo and the residue was purified by flash column chromatography to give the title compound as white powder (0.444 g, 82%). LC/MS m/e calcd. for C27H22BrClFNO3: 541, observed (M+H)+: 542.

Workup

customThe solvent was removed in vacuo
customthe residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-94cd0f6275ad4fcfbee53fbec8d59b7e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354443B2

Reaction notes

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