N-bromobutanimide → Ethyl 4-amino-2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate

HRID 573547Notes

Reaction equation

HRID 573547 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][CH:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[C:3]=12.[Br:25]N1C(=O)CCC1=O>C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([Br:25])=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[C:3]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68323793Ethyl 4-amino-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate

Product 1

HCID 68324129Ethyl 4-amino-2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylateYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 4-amino-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate (865 mg, 2.53 mmol) (Description 14) in DCM (18 mL), was added N-bromosuccinimide (540 mg, 3.03 mmol) and the resulting mixture stirred for 45 min at RT. The mixture was concentrated and purified by chromatography on silica gel, eluting with a gradient of 0-20% ethyl acetate in cyclohexane, to give the title compound (1.02 g). LCMS (A) m/z: 421/423 [M+1]+, Rt 1.57 min (acidic).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by chromatography on silica gel
  3. washeluting with a gradient of 0-20% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-654eb5ac7902461eadfe5cfd6ff0434a
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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