N-bromobutanimide → Ethyl 6-bromo-2-aminobenzo[b]thiophene-3-carboxylate

HRID 1594230Notes

Reaction equation

HRID 1594230 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[S:9][C:10]=1[NH2:11])=[O:5])[CH3:2].[Br:16]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:8]=2[S:9][C:10]=1[NH2:11])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 699464Ethyl 2-amino-1-benzothiophene-3-carboxylate

Product 1

HCID 18422163Ethyl 6-bromo-2-aminobenzo[b]thiophene-3-carboxylateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1c (760 mg, 3.44 mmol) in CHCl3 (10 mL) was added N-bromosuccinimide (673 mg, 3.78 mmol). The resultant mixture was stirred for 1 h, then mixed with saturated NaHCO3 solution (100 mL), and extracted with methylene chloride (100 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 4:1) then provided the title compound (930 mg, 90%) as a yellow solid: MS (ES) m/z 300 (M+H)+; 1H NMR (400 MHz, CDCl3) δ7.96 (d, J=8.8 Hz, 1H), 7.63 (s, 1H), 7.42 (d, J=8.8 Hz, 1H), 6.52 (brs, 2H), 4.42 (q, J=7.2 Hz, 2H), 1.48 (t, J=7.2 Hz, 3H).

Workup

  1. extractionextracted with methylene chloride (100 mL, 3×)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e1c71066ec0d400ca74bd0d879575e48
Source dataset
uspto-grants-2007_11
Patent number
US07300952B2

Reaction notes

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