4-(Dimethylamino)phenylboronic acid → Ethyl N-(3,4-dichlorobenzyl)-5-(4-[N,N-dimethylamino]phenyl)indole-2-carboxylate

HRID 2305583Notes

Reaction equation

HRID 2305583 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5]2.[CH3:25][N:26]([CH3:36])[C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.C(O)C.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:7]1[C:8]2[C:4](=[CH:3][C:2]([C:30]3[CH:31]=[CH:32][C:27]([N:26]([CH3:36])[CH3:25])=[CH:28][CH:29]=3)=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 2

HCID 27343444-(Dimethylamino)phenylboronic acidHCID 22310916Ethyl 5-bromo-N-(3,4dichlorobenzyl)indole-2-carboxylate

Product 1

HCID 18433334Ethyl N-(3,4-dichlorobenzyl)-5-(4-[N,N-dimethylamino]phenyl)indole-2-carboxylateYield 76.2%

Reagents, catalysts & solvents 2

HCID 178527695HCID 178527695, compoundCatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 5-bromo-N-(3,4dichlorobenzyl)indole-2-carboxylate (0.3 g), 4-dimethylaminobenzene boronic acid (0.13 g) and tetrakis triphenylphosphine-palladium(0) (20 mg) were dissolved in degassed toluene/ethanol/2M potassium carbonate (2:2:1) under argon and warmed at 80° C. for 16 hours. The reaction was then cooled to room temperature and partitioned between 2M HCl and ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography using i-hexane-15% ethyl acetate as eluent to give the desired end product as a pale brown solid (0.25 g, 76%); NMR δ(CDCl3) 1.38 (t, 3H), 2.98 (s, 6H), 4.38 (q, 2H), 5.78 (s, 2H), 6.80-7.80 (m, 11H); M/z (+) 467 (M+), 319, 280, 239.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. custompartitioned between 2M HCl and ethyl acetate
  3. dry with materialCombined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9c5c74a6d52a4355b7fb0e1ba884fbf4
Source dataset
uspto-grants-2002_08
Patent number
US06441004B1

Reaction notes

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