Water → HCID 23003278, compound

HRID 396525Notes

Reaction equation

HRID 396525 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=1.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1B(O)O.C(=O)(O)[O-].[Na+].O>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19]([C:26]2[S:25][CH:29]=[CH:28][CH:27]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 23003358HCID 23003358, compound

Product 1

HCID 23003278HCID 23003278, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of methyl[6-chloro-2-(4-bromobenzoyl)-1H-indol-3-yl]acetate (Example 206, 0.40 g, 0.98 mmol), thiophene-2-boronic acid (0.14 g, 1.08 mmol), saturated aqueous sodium bicarbonate (4 ml), and dichlorobis(triphenylphosphine)palladium(II) (70 mg, 0.098 mmol) in DME (15 ml) was refluxed for 3 h. The mixture was poured into water (30 ml), and extracted with ethyl acetate (50 ml×2). The combined extracts were washed with brine (50 ml), dried (MgSO4), and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate-hexane (1:6) to afford 0.33 g (83%) of the title compound as yellow solids.

Workup

  1. temperaturewas refluxed for 3 h
  2. extractionextracted with ethyl acetate (50 ml×2)
  3. washThe combined extracts were washed with brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography
  7. washeluting with ethyl acetate-hexane (1:6)

Sources & evidence

ORD record
ord-6202187cba184536887f1954f7b75afc
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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