N,N'-Dimethylethylenediamine → HCID 58305406, compound

HRID 1805338Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][C:11]3=[O:19])[CH2:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].CNCCNC.I[C:33]1[CH:34]=[C:35]([CH:41]=[CH:42][CH:43]=1)[C:36]([O:38][CH2:39]C)=[O:37]>[Cu]I.C(#N)C>[CH3:39][O:38][C:36](=[O:37])[C:35]1[CH:41]=[CH:42][CH:43]=[C:33]([N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@:10]3([CH2:9][C@H:8]3[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:11]2=[O:19])[CH:34]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.05 mmol, 5.0 mol %), racemic (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one (270 mg, 1.0 mmol), and K2CO3 (276 mg, 2.0 mmol), evacuated, and backfilled with argon. N,N′-Dimethylethylenediamine (11 μL, 0.10 mmol, 10 mol %), ethyl 3-iodobenzoate (278.8 mg, 1.01 mmol), and acetonitrile (1.5 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 80° C. for 23 hours. HPLC monitored the reaction finished. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography column (gradient elution, 5-10% ethyl acetate in petroleum ether) to give the title compound as a yellow powder (290 mg, 72%). LC/MS m/e calcd. for C24H18ClNO3: 403, observed (M+H)+: 404.1.

Workup

customevacuated
customThe Schlenk tube was sealed with a Teflon valve
customThe solvent was removed under reduced pressure
customThe residue was purified by flash column chromatography column (gradient elution, 5-10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-af471ccbd0df47a4abf8e9d1a665bfa6
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354443B2

Reaction notes

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