Cesium carbonate → HCID 89925439, compound

HRID 922472Notes

Reaction equation

HRID 922472 reaction equation
Br[C:2]1[C:6]2[CH:7]=[N:8][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][C:5]=2[N:4]([CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH:3]=1.[CH3:21]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:20][O:19][CH2:18][CH2:17][CH2:16][N:4]1[C:5]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=[CH:7][C:6]=2[C:2]([CH3:21])=[CH:3]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 574072TrimethylboroxineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 89925418HCID 89925418, compound

Product 1

HCID 89925439HCID 89925439, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of ethyl 3-bromo-1-(3-methoxypropyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (1.70 g) in 1,4-dioxane (25 mL) were added trimethylboroxine (2.09 mL), cesium carbonate (4.87 g), 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (X-Phos) (297 mg) and tris(dibenzylideneacetone)dipalladium (228 mg) under argon, and the mixture was stirred at 110° C. for 15 hours. The reaction solution was cooled, and then thereto was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane→ethyl acetate) to give ethyl 1-(3-methoxypropyl)-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate [REx(105-4)] (831 mg) as a yellow oil.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane→ethyl acetate)

Sources & evidence

ORD record
ord-3b9621fbddc5409980ae1880e5cffdc4
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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