Cesium carbonate → HCID 125505030, compound

HRID 1479888Notes

Reaction equation

HRID 1479888 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][N:13]([CH2:16][CH:17]3[CH2:19][CH2:18]3)[CH2:12][CH2:11]2)[N:3]=1.[F:20][C:21]([F:33])([F:32])[O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH:17]1([CH2:16][N:13]2[CH2:14][CH2:15][N:10]([C:4]3[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([C:26]4[CH:25]=[CH:24][C:23]([O:22][C:21]([F:20])([F:32])[F:33])=[CH:28][CH:27]=4)[N:3]=3)[CH2:11][CH2:12]2)[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 83073430HCID 83073430, compound

Product 1

HCID 125505030HCID 125505030, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The nitrile 25D (2.4 g, 8.67 mmol), 4-trifluoromethoxyphenylboronic acid (2.15 g, 1.1 mol eq), palladium acetate (45 mg), cesium carbonate (4.5 g, 2 mol eq), and XPhos (190 mg) were mixed, placed under a nitrogen atmosphere and dioxane (10 mL) was added. The mixture was heated at 100° C. overnight. After cooling, the mixture was filtered through a celite pad, washed with dioxane (2×20 mL) and concentrated under reduced pressure. The residue was used for the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through a celite pad
  3. washwashed with dioxane (2×20 mL)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was used for the next step without further purification

Sources & evidence

ORD record
ord-6b530e8ce79e49b9be4318de28edfd10
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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