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Potassium Phosphate, Tribasic → Ethyl 5-fluoro-1-(4,6-dimethylpyridin-2-yl)-1H-indole-2-carboxylate

HRID 252192
Notes
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Reaction equation

HRID 252192 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.Br[C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[N:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNC1CCCCC1NC>[Cu](I)I.C(OCC)(=O)C.C(O)(=O)C.O.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[N:18]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylateHCID 149751952-Bromo-4,6-dimethylpyridine

Product 1

HCID 66845370Ethyl 5-fluoro-1-(4,6-dimethylpyridin-2-yl)-1H-indole-2-carboxylateYield 84.8%

Reagents, catalysts & solvents

5
HCID 83717Copper iodideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

4.35 g (21 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate, 4.29 g (23.1 mmol) of 2-bromo-4,6-dimethylpyridine, 9.36 g (44.1 mmol) of tripotassium phosphate, 0.66 ml (4.2 mmol) of 1,2-dimethylaminocyclohexane, 0.2 g (1.05 mmol) of copper iodide and 21 ml of dry toluene are added to a pressure tube. The tube is closed and the reaction mixture is stirred at 110° C. for 5 days. After this time, the mixture is poured onto a solution of 100 ml of water and the pH of the medium is adjusted to pH 5 by additions of acetic acid. 100 ml of ethyl acetate are added. The organic phase is separated, washed successively with 50 ml of water and 50 ml of a saturated aqueous sodium chloride solution, then dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue is purified by preparative chromatography (eluent: dichloromethane/ethyl acetate). 5.56 g of expected product are obtained, which product is used as is in the continuation of the synthesis.

Workup

  1. customThe tube is closed
  2. customThe organic phase is separated
  3. washwashed successively with 50 ml of water and 50 ml of a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by preparative chromatography (eluent: dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-f53d76a0370940489ad956c4b9377b92
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07868024B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes