2-Chloro-5-(trifluoromethyl)pyridine → HCID 90159268, compound

HRID 2200082Notes

Reaction equation

HRID 2200082 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:2]1.Cl[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1.CC(C)([O-])C.[Na+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:11]([O:10][C:9](=[O:15])[NH:8][CH2:7][CH:3]1[O:4][CH2:5][CH2:6][N:1]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)[CH2:2]1)([CH3:12])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 19081107tert-Butyl [(morpholin-2-yl)methyl]carbamateHCID 23676156Sodium t-butoxide

Product 1

HCID 90159268HCID 90159268, compound

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl morpholin-2-ylmethylcarbamate (1.0 g, 4.62 mmol), 2-chloro-5-(trifluoromethyl)pyridine (839 mg, 4.62 mmol), Pd(dba)2 (133 mg, 0.23 mmol), sodium tert-butoxide (533 mg, 5.55 mmol) and X-Phos (220 mg, 0.46 mmol) were combined in toluene (10 mL). The mixture was degassed with nitrogen for 5 minutes and sealed. The resulting mixture was stirred at 100° C. for 12 h. The mixture was filtered and rinsed with THF. Solvents were evaporated and the residue was purified by ISCO flash column chromatography (0% to 35% ethyl acetate in hexanes) to give the desired compound as a light brown waxy material (350 mg, 21%). [MH]+=362.1.

Workup

  1. customThe mixture was degassed with nitrogen for 5 minutes
  2. customsealed
  3. filtrationThe mixture was filtered
  4. washrinsed with THF
  5. customSolvents were evaporated
  6. customthe residue was purified by ISCO flash column chromatography (0% to 35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-53eb9396cf7b4363b3a6b10b9aa094bf
Source dataset
uspto-grants-2016_06
Patent number
US09359337B2

Reaction notes

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