Lithium Chloride → Ethyl N-(3,4-dichlorobenzyl)-4-(2-pyridyl)indole-2-carboxylate

HRID 967100Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1.C([Sn](CCCC)(CCCC)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)CCC.[Cl-].[Li+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[CH2:11][N:6]1[C:7]2[C:3](=[C:2]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[CH:10]=[CH:9][CH:8]=2)[CH:4]=[C:5]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

Conditions

Temperature: 105 °C

Procedure

Ethyl 4-bromo-N-(3,4-dichlorobenzyl)indole-2-carboxylate (0.15 g), 2-(tri-n-butylstannyl)pyridine (0.155 g), lithium chloride (30 mg) and tetrakis triphenylphosphine-palladium(0) (15 mg) were dissolved in anhydrous degassed toluene under argon and warmed at 105° C. for 16 hours. The reaction was then cooled to room temperature and partitioned between water and dichloromethane. Combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography using i-hexane-30% ethyl acetate as eluent to give the desired end product as a white solid (0.08 g, 54%); M/z (+) 425 (M+).

Workup

customin anhydrous degassed toluene under argon
temperatureThe reaction was then cooled to room temperature
custompartitioned between water and dichloromethane
dry with materialCombined organic extracts were dried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-f1abbd27260c4ee6a8ac9944d7456f89
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06953809B2

Reaction notes

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