Ethyl Acetate → 7-Bromo-3-(3-chloro-4-fluorophenyl)thieno[3,2-c]pyridin-4-amine

HRID 734312Notes

Reaction equation

HRID 734312 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[C:13]([Cl:18])[CH:12]=3)=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.C1C(=O)N([Br:26])C(=O)C1.[O-]S([O-])=O.[Na+].[Na+].C(OCC)(=O)C>C1COCC1>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[C:13]([Cl:18])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([Br:26])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 114032173-(3-Chloro-4-fluorophenyl)thieno[3,2-c]pyridin-4-amine

Product 1

HCID 113027877-Bromo-3-(3-chloro-4-fluorophenyl)thieno[3,2-c]pyridin-4-amineYield 108.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 4-amino-3-(3-chloro-4-fluoro-phenyl)thieno[3,2-c]pyridine (240 mg, 0.86 mmol) in 10 ml of THF cooled at 0° C. was added NBS (153 mg, 0.86 mmol) and the reaction mixture was stirred for 1 hour at 0° C. The resultant mixture was poured into 10% Na2SO3 and ethyl acetate, the organic phase was collected, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on a silica gel column to afford the titled compound (333 mg). 1H NMR (400 MHz, DMSO-d6) ppm 7.97 (s, 1H), 7.73 (dd, J=2.1, 7.2 Hz, 1H), 7.69 (s, 1H), 7.55 (dd, J=8.8 Hz, 1H), 7.48 (ddd, J=2.2, 4.7, 8.4 Hz, 1H), 5.66 (s, 2H). MS: m/z 357, 359, 361 (M+H)+.

Workup

  1. customthe organic phase was collected
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-709fc161c5c34a469ff8d5a27bb03ff3
Source dataset
uspto-grants-2009_09
Patent number
US07592352B2

Reaction notes

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