Water → 3-(4-(Tert-butyldimethylsilyloxy)cyclohex-1-enyl)-2-fluoropyridine

HRID 1880101Notes

Reaction equation

HRID 1880101 reaction equation
FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][CH:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:9][CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].O.[F:30][C:31]1[C:36](B(O)O)=[CH:35][CH:34]=[CH:33][N:32]=1>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>[Si:14]([O:13][CH:10]1[CH2:11][CH2:12][C:7]([C:36]2[C:31]([F:30])=[N:32][CH:33]=[CH:34][CH:35]=2)=[CH:8][CH2:9]1)([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 534150124-((tert-Butyldimethylsilyl)oxy)cyclohex-1-en-1-yl trifluoromethanesulfonate

Product 1

HCID 593268503-(4-(Tert-butyldimethylsilyloxy)cyclohex-1-enyl)-2-fluoropyridine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

To a sealable vessel was added 4-(tert-butyldimethylsilyloxy)cyclohex-1-enyl trifluoromethanesulfonate (1.90 g, 5.27 mmol), sodium carbonate as a 2N solution in water (7.91 mL, 15.81 mmol), and 2-fluoropyridin-3-ylboronic acid (0.891 g, 6.33 mmol) before adding tetrakis(triphenylphosphine)palladium(0) (0.305 g, 0.264 mmol) under argon. The reaction mixture was sealed and set stirring at 80° C. After complete consumption of starting material, the black mixture was diluted with water before extracting with dichloromethane, drying over sodium sulfate, filtering, and concentrating under reduced pressure to an orange oil, which was used without purification. MS (ESI, pos. ion) m/z: 308.0 (M+1).

Workup

  1. customThe reaction mixture was sealed
  2. customAfter complete consumption of starting material
  3. additionthe black mixture was diluted with water
  4. extractionbefore extracting with dichloromethane
  5. dry with materialdrying over sodium sulfate
  6. filtrationfiltering
  7. concentrationconcentrating under reduced pressure to an orange oil, which
  8. customwas used without purification

Sources & evidence

ORD record
ord-1c9350253c5143dd918a2e7efdc3f637
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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