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

HRID 410234
Notes
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Reaction equation

HRID 410234 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 178418397
HCID 178418397, compound
Catalyst

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-531b8903f9fb45579fac7071e75520d7
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08759532B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes