3-Nitrophenol → HCID 58832946, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([O:19][C:20]([C:22]1[C:23]2[S:31][CH:30]=[C:29]([CH2:32]Br)[C:24]=2[C:25]([Cl:28])=[N:26][CH:27]=1)=[O:21])[CH3:18]>C1COCC1.CN(C=O)C>[CH2:17]([O:19][C:20]([C:22]1[C:23]2[S:31][CH:30]=[C:29]([CH2:32][O:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[C:24]=2[C:25]([Cl:28])=[N:26][CH:27]=1)=[O:21])[CH3:18]Participants
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 3-nitrophenol (457 mg, 3.29 mmol) (Aldrich) and potassium carbonate powder (498 mg, 3.60 mmol) in dry THF (10 mL) and DMF (5 mL) was stirred at 50° C. for 15 minutes before a solution of 3-bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (1.00 g, 2.99 mmol) (from Example 1 supra) in THF (8+2 mL) was added. The reaction was stirred at 50° C. for 3 hours and the resulting mixture was concentrated to remove most of the solvent. The residue was dissolved in EtOAc (200 mL), washed with water (2×25 mL) and brine (25 mL), dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (CH2Cl2/MeOH, 98/2 to 90/10) to give 4-chloro-3-(3-nitro-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white solid. (Yield 911 mg, 78%).
Workup
- additionwas added
- concentrationthe resulting mixture was concentrated
- customto remove most of the solvent
- dissolutionThe residue was dissolved in EtOAc (200 mL)
- washwashed with water (2×25 mL) and brine (25 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe crude product was purified by column chromatography (CH2Cl2/MeOH, 98/2 to 90/10)
Sources & evidence
- ORD record
- ord-35fe05f7a07b450796ded55bd50934fc
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07994321B2
Reaction notes
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