Triethylamine → HCID 89826351, compound

HRID 1485008Notes

Reaction equation

HRID 1485008 reaction equation
[CH3:1][S:2][C:3]1[N:11]=[C:6]2[NH:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][N:14]=1.C(N(CC)CC)C>C1C=CC=CC=1>[Cl:12][C:13]1[N:14]=[CH:15][C:16]([CH2:19][N:7]2[CH:8]=[CH:9][CH:10]=[C:5]3[N:4]=[C:3]([S:2][CH3:1])[N:11]=[C:6]23)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 178503349HCID 178503349, compound

Product 1

HCID 89826351HCID 89826351, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 2-methylsulfanyl-4H-imidazo[4,5-b]pyridine (900 mg, 5.45 mmol), 2-chloro-5-(chloromethyl)pyridine (1.32 g, 8.17 mmol) and triethylamine (1.1 mL, 8.17 mmol) in benzene (18 mL) was stirred at 100° C. for 12 h (microwave). After cooling to room temperature the benzene was decanted off and the resulting solid was triturated with boiling benzene (3×15 mL). The benzene phases were combined and the solvent was removed under reduced pressure. The resulting solid was triturated with CH2Cl2, filtered and dried under reduced pressure to yield 760 mg (2.62 mmol, 48%) of compound E1.4.

Workup

  1. customwas decanted off
  2. customthe resulting solid was triturated with boiling benzene (3×15 mL)
  3. customthe solvent was removed under reduced pressure
  4. customThe resulting solid was triturated with CH2Cl2
  5. filtrationfiltered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-7021f3dd74c4455f9a1100a5cb74347e
Source dataset
uspto-grants-2016_08
Patent number
US09422280B2

Reaction notes

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