Sodium Carbonate → HCID 86596051, compound

HRID 860576Notes

Reaction equation

HRID 860576 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[C:10]12([C:20]3[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][C:25]=3[O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.C(OCC)(=O)C>[C:10]12([C:20]3[CH:21]=[C:22]([C:2]4[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=4)[CH:23]=[CH:24][C:25]=3[O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:28])[CH3:29])[CH2:11][CH:12]3[CH2:18][CH:16]([CH2:15][CH:14]([CH2:13]3)[CH2:19]1)[CH2:17]2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 117692346-Bromo-3-pyridinecarboxaldehydeHCID 69583782HCID 69583782, compound

Product 1

HCID 86596051HCID 86596051, compoundYield 56,989%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 6-bromopyridine-3-carboxaldehyde (15.00 g, 0.0806 mol), 3-adamantan-1-yl-4-t-butyldimethylsilanyloxyphenyl boronic acid (37.39 g, 0.09677 mmol) and sodium carbonate (1.719 g, 12.44 mmol) in 750 mL of toluene:EtOH (4:1) and 75 mL of water was degassed with argon for 30 minutes. Tetrakis(triphenyl-phosphine)palladium(0) (2.335 g, 0.00202 mmol, 0.025 eq) was added and the mixture heated at reflux under argon overnight. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: hexane:ethyl acetate, 9:1) to give 24.689 g of 6-[3-(1-adamantyl)-4-t-butyldimethylsilanyloxyphenyl]-pyridin-3-carboxaldehyde (68%). 1H NMR (300 MHz; CDCl3): δ 0.39 (s, 6H), 1.06 (s, 9H), 1.79 (brs, 6H), [2.11 (brs), 2.19 (s), 9 H], 6.91 (d, J=8.4 Hz, 1H), 7.75–7.85 (m, 2H), 8.04 (d, J=2.1 Hz, 1H), 8.16 (dd, J1=8.4, J2=2.1 Hz, 1H), 9.06(d, J=2.1 Hz, 1H), 10.09 (s, 1H).

Workup

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon overnight
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (eluent: hexane:ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-fe2e91e5ebf24933858e3a8306efb5a9
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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