N-bromobutanimide → tert-Butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

HRID 1713172Notes

Reaction equation

HRID 1713172 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][CH:15]=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:24])C(=O)C1>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([Br:24])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18377286tert-butyl 4H,5H,6H,7H-thieno[3,2-c]pyridine-5-carboxylate

Product 1

HCID 19365864tert-Butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6,7-dihydro-4H-thieno[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (240 mg, 1.0 mmol) in acetonitrile (5 ml) cooled to 0° C. is added NBS (183 mg, 1.03 mmol, 1.03 eq.). The mixture is stirred at rt overnight. The organic phase is collected, washed with water (10 ml) and brine (10 ml), dried over sodium sulfate, and concentrated. The residue is purified by silica gel chromatography (hexane/EtOAc 10:1) to give the title compound. MS (+VE) m/z 318.1 (M++1).

Workup

  1. customThe organic phase is collected
  2. washwashed with water (10 ml) and brine (10 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel chromatography (hexane/EtOAc 10:1)

Sources & evidence

ORD record
ord-173f76f8558e40e4ab0f8618c7e1341b
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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