Water → HCID 125505436, compound

HRID 1479829Notes

Reaction equation

HRID 1479829 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:3]=1.O.C(=O)(O)[O-].[Na+].[F:22][C:23]([F:35])([F:34])[O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>C(COC)OC>[O:13]1[CH2:14][CH2:15][N:10]([C:4]2[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([C:28]3[CH:27]=[CH:26][C:25]([O:24][C:23]([F:22])([F:34])[F:35])=[CH:30][CH:29]=3)[N:3]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 830745812-Chloro-6-morpholin-4-yl-isonicotinonitrile

Product 1

HCID 125505436HCID 125505436, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The carbonitrile 25B (2.3 g, 10.28 mmol) was dissolved in 80 ml of dimethoxyethane. To the solution were added 40 ml of water, sodium bicarbonate (3 equiv., 2.6 g), [4-(trifluoromethoxy)phenyl]boronic acid (1.2 equiv., 2.54 g) and the mixture was stirred at rt for 5′. The mixture was degassed and put under argon. A catalytic amount of tetrakispalladium was added and the mixture was heated at 100° C. overnight. The solvents were evaporated off and the residue was dissolved with ethyl acetate, washed with water and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The crude was crystallized from ethyl acetate and petroleum ether to give a beige solid. (2.0 g, 55.5% yield)1HNMR (DMSO, 400 MHz) δ 3.61 (4H, m), 3.72 (4H, m), 7.20 (1H, s), 7.79 (1H, s), 7.82 (2H, d, J=8 Hz), 8.35 (2H, d, J=8 Hz)

Workup

  1. customThe mixture was degassed
  2. additionA catalytic amount of tetrakispalladium was added
  3. temperaturethe mixture was heated at 100° C. overnight
  4. customThe solvents were evaporated off
  5. dissolutionthe residue was dissolved with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe crude was crystallized from ethyl acetate and petroleum ether
  10. customto give a beige solid

Sources & evidence

ORD record
ord-3cfe03f625f24131aadbb3e38284940b
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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