N-bromobutanimide → Ethyl 4-amino-2-bromo-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate

HRID 573556Notes

Reaction equation

HRID 573556 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]([CH3:17])[C:3]=12.[Br:18]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:18])=[C:16]([CH3:17])[C:3]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68323726Ethyl 4-amino-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate

Product 1

HCID 68324019Ethyl 4-amino-2-bromo-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylateYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 4-amino-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate (210 mg, 0.839 mmol) (Description 30) in DCM (4 mL), was added N-bromosuccinimide (164 mg, 0.923 mmol) and the resulting mixture stirred for 20 min at RT. The mixture was concentrated and purified by chromatography on silica gel, eluting with a gradient of 0-50% ethyl acetate in cyclohexane, to afford the title compound (261 mg). LCMS (A) m/z: 329/331 [M+1]+, Rt 1.20 min (acidic).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by chromatography on silica gel
  3. washeluting with a gradient of 0-50% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-451e2dfb3d2f4bc28f9818531bfedd0a
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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