Sodium Carbonate → HCID 21833078, compound

HRID 1740813Notes

Reaction equation

HRID 1740813 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[N:8]([C:16](=[O:24])[NH:17][C:18]1[S:19][C:20](Br)=[CH:21][CH:22]=1)[CH2:7][CH2:6]2.C(=O)([O-])[O-].[Na+].[Na+].N1C=CC=C(B(O)O)C=1>C(COC)OC.O.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>[S:19]1[CH:20]=[CH:21][CH:22]=[C:18]1[NH:17][C:16]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([C:12]([F:13])([F:14])[F:15])[CH:10]=2)[CH2:6][CH2:7]1)=[O:24]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 21833115HCID 21833115, compound

Product 1

HCID 21833078HCID 21833078, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

A mixture of 5-methoxy-6-trifluoromethyl-1-(5-bromo-2-thienyl) carbamoyl indoline (E48) (0.64 g, 1.5 mmol), sodium carbonate (1.1 g), pyridine-3-boronic acid (0.55 g, 4.5 mmol) and tetrakis triphenylphine palladium(0) (0.1 g) in dimethoxyethane/water (20 ml/5 ml) was heated to reflux overnight under argon. Extraction workup and chromatography afforded the title compound in 27% yield as a white solid, m.p. 240-244° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight under argon
  3. extractionExtraction workup and chromatography

Sources & evidence

ORD record
ord-52a52102af9f4a609277b3d204a2ff2b
Source dataset
uspto-grants-1999_10
Patent number
US05972937

Reaction notes

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