Cesium carbonate → HCID 89925481, compound

HRID 922477Notes

Reaction equation

HRID 922477 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.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:27]1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCC[CH2:28]1>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]>[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]([CH:27]=[CH2:28])=[CH:3]1

Participants

6

Reactant 3

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

Product 1

HCID 89925481HCID 89925481, compoundYield 348.4%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 3-bromo-1-(3-methoxypropyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (200 mg) in 1,4-dioxane (2 mL) were added trivinylboroxine pyridine complex (141 mg), cesium carbonate (573 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (X-Phos) (56 mg) and tris(dibenzylideneacetone)dipalladium (27 mg) under argon, and the mixture was stirred at 100° C. for 1 hour. The reaction solution was cooled, and then thereto 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=9/1→4/1) to give ethyl 1-(3-methoxypropyl)-3-vinyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate [REx(106-1)] (118 mg) as a yellow oil.

Workup

  1. temperatureThe reaction solution was cooled
  2. washwas washed with saturated saline
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1→4/1)

Sources & evidence

ORD record
ord-029830b33b084154b454fee8ad2200d0
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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