Cesium fluoride → HCID 86725270, compound

HRID 576647Notes

Reaction equation

HRID 576647 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:5]2=[N:6][CH:7]=1.[F-].[Cs+].[CH2:20](B1OC(C)(C)C(C)(C)O1)[CH:21]=[CH2:22]>C1COCC1.CCOCC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:22]([C:2]1[CH:3]=[C:4]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:5]2=[N:6][CH:7]=1)[CH:21]=[CH2:20]

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 27631714,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolaneHCID 72214604HCID 72214604, compound

Product 1

HCID 86725270HCID 86725270, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 3-bromo-5,7-dihydropyrrolo[3,4-b]pyridine-6-carboxylate (857 mg, 2.87 mmol), cesium fluoride (1.7 g, 11.5 mmol), and tetrakis-(triphenylphosphine) palladium (0) (229 mg, 0.2 mmol) in THF (15 mL) was degassed and flushed with nitrogen. To this mixture was added allyl-boronic acid pinacol ester (820 μL, 4.3 mmol). The resulting mixture was heated to reflux and stirred at this temperature for 2.5 hr then cooled to room temperature, diluted with ether, washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by silica chromatography (25 g silica, eluted with 5-40% ethyl acetate in hexanes) to give the title compound as a solid.

Workup

  1. customwas degassed
  2. customflushed with nitrogen
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica chromatography (25 g silica, eluted with 5-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-516d05df12724a74917edd39ce4e83c5
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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