Water → HCID 57619448, compound

HRID 1754746Notes

Reaction equation

HRID 1754746 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-a05672308bce458a92e14c1d47c321d7
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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