Water → HCID 43114359, compound

HRID 1916597Notes

Reaction equation

HRID 1916597 reaction equation
[Cl:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.C(N(CC)CC)C.O>C(Cl)Cl>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:3](=[O:4])[CH:2]([Cl:1])[CH3:6])=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 706222-Amino-5-bromopyridineHCID 1110192-Chloropropionyl chloride2×

Product 1

HCID 43114359HCID 43114359, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.14 mL (22.0 mmol) 2-chloropropionic acid chloride in 5 mL DCM is added dropwise to a solution of 3.46 g (20.0 mmol) 2-amino-5-bromopyridine and 6.12 mL (44.0 mmol) triethylamine in 80 mL DCM at 0° C. The ice bath is removed and the reaction solution is stirred for a further 1.5 h at RT. Another 0.40 mL (4.12 mmol) 2-chloropropionic acid chloride is added and the solution is stirred for a further hour at RT. The reaction mixture is combined with 80 mL water, washed once with 80 mL saturated NaCl solution and dried over MgSO4. The solvent is eliminated i.vac. and the residue is triturated with a little EtOAc, suction filtered and dried.

Workup

  1. customThe ice bath is removed
  2. stirringthe solution is stirred for a further hour at RT
  3. washwashed once with 80 mL saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customand the residue is triturated with a little EtOAc, suction
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-bba948386728496d8f7cafebb5a1fb4b
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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