Sodium Carbonate → 2-(2-Methoxy-3-nitro-phenyl)-5-methyl-thiazole-4-carboxylic acid

HRID 384388ノート

反応式

HRID 384388 の反応式
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1B1OC(C)(C)C(C)(C)O1.Br[C:22]1[S:23][C:24]([CH3:30])=[C:25]([C:27]([OH:29])=[O:28])[N:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:22]1[S:23][C:24]([CH3:30])=[C:25]([C:27]([OH:29])=[O:28])[N:26]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 534458932-Bromo-5-methyl-1,3-thiazole-4-carboxylic acidHCID 574838002-(2-Methoxy-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 574838392-(2-Methoxy-3-nitro-phenyl)-5-methyl-thiazole-4-carboxylic acid収率 26%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

2-(2-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 6a (1.7 g, 6.08 mmol), 2-bromo-5-methyl-thiazole-4-carboxylic acid (900 mg, 4.05 mmol), tetrakis(triphenylphosphine)palladium (233 mg, 0.2 mmol) and sodium carbonate (1.29 g, 12.16 mmol) were dissolved in 30 mL of 1,4-dioxane. The reaction mixture was heated to reflux for 4 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was diluted with 20 mL of hydrochloric acid (1 N) and 30 mL of ethyl acetate. The separated organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was recrystallized from a solvent mixture of ethyl acetate and hexane to obtain the title compound 2-(2-methoxy-3-nitro-phenyl)-5-methyl-thiazole-4-carboxylic acid 47a (310 mg, yield 26%) as a yellow solid.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionThe residue was diluted with 20 mL of hydrochloric acid (1 N) and 30 mL of ethyl acetate
  6. washThe separated organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customto remove the drying agent
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was recrystallized from a solvent mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-c64bc98a077d4c3e872e56ccf20810b3
出典データセット
uspto-grants-2013_02
特許番号
US08367710B2

反応ノート

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