Morpholine → HCID 68283965, compound

HRID 1527485Notes

Reaction equation

HRID 1527485 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:11])[C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:11][C:4]1[C:5]([F:10])=[C:6]([CH:9]=[C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:3]=1)[C:7]#[N:8]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 265983415-Bromo-3-chloro-2-fluorobenzonitrile

Product 1

HCID 68283965HCID 68283965, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 5-Bromo-3-chloro-2-fluoro-benzonitrile (200 mg, 0.85 mmol), morpholine (74 mg, 0.85 mmol), caesium carbonate (389 mg, 1.2 mmol), palladium(II) acetate (10 mg, 0.04 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (35 mg, 0.06 mmol) in toluene (5 mL) was sealed in a microwave vial and heated for 30 min at 140° C. (Emrys Optimizer; personal chemistry). The reaction mixture was quenched by addition of saturated aqueous NaHCO3, extracted with EtOAc, dried (Na2SO4) and the solvent was removed in vacuo to give the title compound which was used without further purification in the next step. TLC Rf (hexane/EtOAc 1:1)=0.60; tR (HPLC conditions c): 5.28 min.

Workup

  1. customwas sealed in a microwave vial
  2. customThe reaction mixture was quenched by addition of saturated aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3d81bc460e294c2eb2309e8ede77bda3
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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