N-bromobutanimide → HCID 68324025, compound

HRID 573569Notes

Reaction equation

HRID 573569 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]([Br:23])[CH:18]=3)[C:3]=12.[Br:24]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:24])=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=3)[C:3]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68324059HCID 68324059, compound

Product 1

HCID 68324025HCID 68324025, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-amino-3-(3-bromophenyl)-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 46) (6.309 g, 16.12 mmol) in DCM (100 mL) was added N-bromosuccinimide (3.44 g, 19.35 mmol) at RT. The mixture was stirred for 3.5 h. The solvent was removed in vacuo. The crude residue was then purified by chromatography on silica, eluting with a gradient of 0-30% ethyl acetate in cyclohexane, to give the title compound (5.13 g). LCMS (A) m/z: 471 [M+1]+, Rt 1.52 min (acidic).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude residue was then purified by chromatography on silica
  3. washeluting with a gradient of 0-30% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-f389b60996384fa3839ed251c98af3dc
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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