Sodium Bicarbonate → HCID 90391307, compound

HRID 1479833Notes

Reaction equation

HRID 1479833 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:3]=1.[F:15][C:16]([F:28])([F:27])[O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>COCCOC.O>[N:10]1([C:4]2[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([C:21]3[CH:20]=[CH:19][C:18]([O:17][C:16]([F:15])([F:27])[F:28])=[CH:23][CH:22]=3)[N:3]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 830745802-Chloro-6-(pyrrolidin-1-yl)pyridine-4-carbonitrile

Product 1

HCID 90391307HCID 90391307, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of nitrile 25A (2.58 g, 12.5 mmol) in DME (90 mL) was added with 4-trifluoromethoxy phenyl boronic acid (2.64 g, 1.0 mol eq,) and NaHCO3 (3.15 g, 3 mol eq,) suspended in water (45 mL). The mixture was degassed under vacuum, then Palladium Tetrakis was added (catalytic amount) and the reaction was stirred at 100° C. under inert atmosphere for 12 h. The solvent was removed under reduced pressure and water was added to the residue (80 mL). The aqueous phase was extracted with EtOAc (3×60 mL) and the combined organic layer was washed with brine (80 mL) and dried over Na2SO4. The solvent was evaporated under vacuum to afford 26C as deliquescent yellow solid (3.2 g, 9.6 mmol, 77% Yield). 1HNMR (DMSO, 400 MHz) δ 1.85 (m, 4H), 3.42 (m, 4H), 6.38 (s, 1H), 7.08 (s, 1H), 7.38 (d, 2H, J=8), 8.05 (d, 2H, J=8).

Workup

  1. customThe mixture was degassed under vacuum
  2. additionPalladium Tetrakis was added (catalytic amount)
  3. customThe solvent was removed under reduced pressure and water
  4. additionwas added to the residue (80 mL)
  5. extractionThe aqueous phase was extracted with EtOAc (3×60 mL)
  6. washthe combined organic layer was washed with brine (80 mL)
  7. dry with materialdried over Na2SO4
  8. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-084463b54b1a49479a6862e8155bae12
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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