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

HRID 967100
Notes
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Reaction equation

HRID 967100 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 6077842-(Tributylstannyl)pyridineHCID 22311024Ethyl 4-bromo-N-(3,4-dichlorobenzyl)indole-2-carboxylate

Product 1

HCID 22311015Ethyl N-(3,4-dichlorobenzyl)-4-(2-pyridyl)indole-2-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 178527695
HCID 178527695, compound
Catalyst

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

  1. customin anhydrous degassed toluene under argon
  2. temperatureThe reaction was then cooled to room temperature
  3. custompartitioned between water and dichloromethane
  4. dry with materialCombined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes