Triethylamine → HCID 86641477, compound

HRID 472758Notes

Reaction equation

HRID 472758 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[CH:3]=1.[Br:10][CH2:11][C:12](Br)=[O:13].C(N(CC)CC)C>C(Cl)Cl>[Br:10][CH2:11][C:12]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[CH:3]=1)=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 1376524-Amino-2,6-dichloropyridine

Product 1

HCID 86641477HCID 86641477, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 4-amino-2,6-dichloro-pyridine (4.7 g, 28.8 mmol) in DCM, bromoacetyl bromide (2.56 ml, 29.4 mmol) is added. The solution is cooled to 0° C. and stirred for 5 minutes before treating dropwise with triethylamine (7.87 ml, 57.7 mmol). The reaction mixture is gradually allowed to warm to RT and stirred for 48 hours. The reaction mixture is diluted with DCM and washed with water several times. The organic extracts are dried, filtered and concentrated in vacuo. The crude product is purified using flash column chromatography on silica (DCM/Isohexane) to afford the title compound.

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 48 hours
  3. washwashed with water several times
  4. customThe organic extracts are dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified

Sources & evidence

ORD record
ord-4599cebc337b491aba1ae3e2ca15003e
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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