Citric Acid → 5-tert-butyl-1-(2'-chloro-1,1'-biphenyl-3-yl)-1H-pyrazole-3-carboxylic acid

HRID 733127

反応式

HRID 733127 の反応式
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][C:10]([C:17]([O:19]CC)=[O:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:13]([C:12]1[N:8]([C:4]2[CH:3]=[C:2]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[Cl:22])[CH:7]=[CH:6][CH:5]=2)[N:9]=[C:10]([C:17]([OH:19])=[O:18])[CH:11]=1)([CH3:15])([CH3:16])[CH3:14]

参加物

10

反応物 6

HCID 311Citric AcidHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 27343222-Chlorophenylboronic acidHCID 57428253ethyl 1-(3-bromophenyl)-5-tert-butyl-1H-pyrazole-3-carboxylate

生成物 1

HCID 112796905-tert-butyl-1-(2'-chloro-1,1'-biphenyl-3-yl)-1H-pyrazole-3-carboxylic acid

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 10311-Propanol溶媒

実験手順

To a solution of ethyl 1-(3-bromophenyl)-5-tert-butyl-1H-pyrazole-3-carboxylate and 2-chlorophenylboronic acid (0.279 g, 1.78 mmol) in n-propanol:water (2.35 ml:0.482 ml) mixture were added palladium acetate (0.005 g), triphenylphosphine (0.016 g) and 2N sodium carbonate (0.497 ml) and the solution was refluxed for 16 hours. To the reaction, a 2N solution of NaOH (1.5 ml) was added and refluxed for an additional 2 hours. The solution was cooled, acidified with 10% citric acid and extracted into ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give 0.212 g of 5-tert-butyl-1-(2′-chloro-1,1′-biphenyl-3-yl)-1H-pyrazole-3-carboxylic acid.

後処理

  1. temperaturethe solution was refluxed for 16 hours
  2. customTo the reaction
  3. temperaturerefluxed for an additional 2 hours
  4. temperatureThe solution was cooled
  5. extractionextracted into ethyl acetate
  6. washThe organic phase was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-3b54fcb58b5f418dbddf2a237380cde7
出典データセット
uspto-grants-2009_09
特許番号
US07589116B2

関連ノート

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