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

HRID 573540Notes

Reaction equation

HRID 573540 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][C:15]([CH3:17])=[CH:16][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]([CH3:17])=[C:16]([Br:18])[C:3]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68323856Ethyl 4-amino-2,6-dimethylthieno[2,3-b]pyridine-5-carboxylate

Product 1

HCID 68323712Ethyl 4-amino-3-bromo-2,6-dimethylthieno[2,3-b]pyridine-5-carboxylateYield 111.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 4-amino-2,6-dimethylthieno[2,3-b]pyridine-5-carboxylate (6.44 g, 25.7 mmol) (Description 5) in DCM (110 mL), was added N-bromosuccinimide (9.16 g, 51.5 mmol) and the resulting mixture was stirred for 1 h. The mixture was concentrated and the solid that precipitated was filtered and washed with DCM (3×10 mL), to afford the title compound (9.44 g). LCMS (A) m/z: 329/331 [M+1]+, Rt 1.22 min (acidic).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe solid that precipitated
  3. filtrationwas filtered
  4. washwashed with DCM (3×10 mL)

Sources & evidence

ORD record
ord-a73b8cff4a154c3086994438615145b2
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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