N,N'-Dimethylethylenediamine → 1-(4-Isopropoxyphenyl)-5-(6-isopropoxypyrid-3-yl)indole-2-carb-oxylic acid ethyl ester

HRID 646105Notes

Reaction equation

CNCCNC.[CH2:7]([O:9][C:10]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([C:21]1[CH:22]=[N:23][C:24]([O:27][CH:28]([CH3:30])[CH3:29])=[CH:25][CH:26]=1)=[CH:16][CH:15]=2)=[O:11])[CH3:8].Br[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:41])[CH3:40])=[CH:34][CH:33]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.C1(C)C=CC=CC=1>[CH2:7]([O:9][C:10]([C:12]1[N:13]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:41])[CH3:40])=[CH:34][CH:33]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([C:21]1[CH:22]=[N:23][C:24]([O:27][CH:28]([CH3:29])[CH3:30])=[CH:25][CH:26]=1)=[CH:16][CH:15]=2)=[O:11])[CH3:8]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of CuI (7.14 mg, 51 mmol), N,N′-dimethyl-1,2-diaminoethane (16.7 μL, 0.153 mmol) and toluene (0.5 mL) was added to a mixture of 5-(6-isopropoxypyrid-3-yl)indole-2-carboxylic acid ethyl ester (165 mg, 0.510 mmol; see step (a)), 1-bromo-4-isopropoxybenzene (219 mg, 1.02 mmol), K3PO4 (108 mg, 0.510 mmol) and toluene (2 mL) under argon. The mixtures was heated at 110° C. for 5 h and at 140° C. for 16 h, then allowed to cool to room temperature and filtered through Celite®. The filter cake was washed with EtOAc and the combined filtrates were concentrated and purified by chromatography to give the sub-title compound (163 mg, 70%).

Workup

temperatureto cool to room temperature
filtrationfiltered through Celite®
washThe filter cake was washed with EtOAc
concentrationthe combined filtrates were concentrated
custompurified by chromatography

Sources & evidence

ORD record: ord-74250d38cf034607bba27150bbd648bc
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705023B2

Reaction notes

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