Potassium Carbonate → HCID 58001758, compound

HRID 420716Notes

Reaction equation

HRID 420716 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[F:10].[C:11]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.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>[F:10][C:3]1[CH:4]=[C:5]([CH2:8][OH:9])[CH:6]=[N:7][C:2]=1[CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 58001772HCID 58001772, compound

Product 1

HCID 58001758HCID 58001758, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (6-chloro-5-fluoro-3-pyridinyl)methanol (1.3 g, 8.05 mmol) in 1,4-dioxane (10 ml) was added K2CO3 (3.34 g, 24.14 mmol), trimethylboroxin (1.125 ml, 8.05 mmol) and Pd(PPh3)4 (0.465 g, 0.402 mmol). The mixture was then heated at 110° C. for 20 h in a pressure tube. The resulting mixture was quenched with H2O, extracted with EtOAc, dried over MgSO4 and concentrated under vacuum. The residue was purified by flash chromatography using Flashmaster II, a 25 g spherical silica gel cartridge and DCM/MeOH 98:2 as eluent to give 560 mg of the title compound along with Ph3PO. This was washed again with water and extracted with EtOAc to remove Ph3PO. The organic layer was dried over MgSO4, filtered and concentrated under vacuum to give 468 mg (39%) of the title compound pure enough to be used in the next step.

Workup

  1. customThe resulting mixture was quenched with H2O
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2aedddb6391b4cf2b7ed50541467c3c4
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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