Water → HCID 17965116, compound

HRID 509954Notes

Reaction equation

HRID 509954 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.C(N(CC)C(C)C)(C)C.O>CN1CCCC1=O>[F:8][C:4]1[N:3]=[C:2]([NH:16][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 739342,6-DifluoropyridineHCID 754524-MethoxybenzylamineHCID 81531Diisopropylethylamine

Product 1

HCID 17965116HCID 17965116, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To 2,6-difluoro-pyridine (49, 100 g, 869 mmol) in 500 mL of N-methylpyrrolidinone, 4-methoxy-benzylamine (77, 136 mL, 1.043 mol) and N,N-diisopropylethylamine (304 mL, 1.738 mol) were added. The reaction was stirred at 90° C. overnight, then poured into 8 L of water. The precipitate collected by filtration and washed with water, then taken up in ethyl acetate and washed with water. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was triturated with heptane and collected by filtration to provide the desired compound (78, 151 g, 650 mmol, 74.8% yield).

Workup

  1. filtrationThe precipitate collected by filtration
  2. washwashed with water
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material was triturated with heptane
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6cfbb0f0bb3c4618852c47d4c2219526
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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