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

HRID 1244094Notes

Reaction equation

HRID 1244094 reaction equation
[H-].[Na+].C(O[C:6]([C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)=[C:11]([Cl:20])[S:10][C:9]=1[NH:21][C:22](=[O:26])[CH2:23][C:24]#[N:25])=[O:7])C.Cl>O1CCCC1>[Cl:20][C:11]1[S:10][C:9]2[NH:21][C:22](=[O:26])[C:23]([C:24]#[N:25])=[C:6]([OH:7])[C:8]=2[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([Br:19])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 696073704-(4-Bromophenyl)-5-chloro-2-(2-cyano-acetylamino)-thiophene-3-carboxylic acid ethyl ester

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 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (1.33 g, 33.2 mmol, 60% dispersion in mineral oil) in tetrahydrofuran (60 mL) at room temperature was added a solution of 4-(4-bromophenyl)-5-chloro-2-(2-cyano-acetylamino)-thiophene-3-carboxylic acid ethyl ester (5.26 g, 12.3 mmol) in tetrahydrofuran (60 mL) over 15 minutes. The reaction was stirred at room temperature for 12 h, and 1 N HCl was added (15 mL). The reaction was then concentrated under reduced pressure, and the resulting solid was triturated with water (15 mL) and diethyl ether (20 mL) to provide the titled compound. MS (APCI) m/e 381 (M−H)−.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. customthe resulting solid was triturated with water (15 mL) and diethyl ether (20 mL)

Sources & evidence

ORD record
ord-a597eb01d90f443eb10e8a12ebdcfaeb
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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