Water → HCID 57619448, compound

HRID 1952124Notes

Reaction equation

HRID 1952124 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=2)[CH:5]=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O.O>C(#N)C>[Br:20][C:3]1[CH:4]=[CH:5][C:6]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:14][CH:15]=2)=[N:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 57619409HCID 57619409, compound

Product 1

HCID 57619448HCID 57619448, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To (6-chloro-pyridin-2-yl)-(6-trifluoromethyl-pyridin-3-ylmethyl)-amine (567, 4.50 g, 0.0156 mol) in acetonitrile (120.0 mL) under an atmosphere of nitrogen, N-bromosuccinimide (3.03 g, 0.0170 mol) in acetonitrile (50 mL) was added slowly. The reaction was stirred at room temperature overnight, then poured into water, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and purified with silica gel column chromatography eluting with 25% to 100% ethyl acetate in hexane to give a white solid (568, 6.20 g, 80.2%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified with silica gel column chromatography
  5. washeluting with 25% to 100% ethyl acetate in hexane
  6. customto give a white solid (568, 6.20 g, 80.2%)

Sources & evidence

ORD record
ord-5f4b6988130344d1915d744cf79a38fb
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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