N-chlorosuccinamide → 2-Chloro-4-hydroxy-3-(4-bromophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

HRID 1244123Notes

Reaction equation

HRID 1244123 reaction equation
[Cl:1]NC(=O)CCC(N)=O.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:25]3[C:24]([OH:26])=[C:23]([C:27]#[N:28])[C:22](=[O:29])[NH:21][C:20]=3[S:19][CH:18]=2)=[CH:13][CH:12]=1>C(O)(=O)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:25]3[C:24]([OH:26])=[C:23]([C:27]#[N:28])[C:22](=[O:29])[NH:21][C:20]=3[S:19][C:18]=2[Cl:1])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 15238416N-chlorosuccinamideHCID 546964233-(4-Bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

Product 1

HCID 546898652-Chloro-4-hydroxy-3-(4-bromophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

N-chlorosuccinamide (1.56 mmol, 0.2 g) was added to a solution of 3-(4-bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (1 mmol, 0.350 g) in acetic acid (5 mL) at room temperature. The reaction was heated at 90° C. for 5 h, cooled and quenched with water (30 mL). The aqueous mixture was extracted with ethyl acetate (3×30 mL), dried (Na2SO4), concentrated and purified on RP-HPLC to afford the title compound. MS (ESI) m/e 381 (M−H)+; 1H NMR (500 MHz, DMSO-d6): δ ppm 11.93 (br s, 1H), 7.59 (d, J=10, 2H), 7.28 (d, J=10, 2H).

Workup

  1. temperaturecooled
  2. customquenched with water (30 mL)
  3. extractionThe aqueous mixture was extracted with ethyl acetate (3×30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified on RP-HPLC

Sources & evidence

ORD record
ord-d2b48efd0dac4617bda36ba7c1662669
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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