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Hydrochloric Acid → 3-(2-hydroxy-4-methoxy-5-(1-methyl-1H-indazol-5-yl)phenyl)propanoic acid

HRID 2194947
ノート
印刷プレビュー

反応式

HRID 2194947 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][C:7](=[O:14])[CH2:6][CH2:5]2.[CH3:15][N:16]1[C:24]2[C:19](=[CH:20][C:21](B(O)O)=[CH:22][CH:23]=2)[CH:18]=[N:17]1.C(=O)([O-])[O-:29].[K+].[K+].[OH-].[Na+].Cl>C(COC)OC.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.O>[OH:8][C:9]1[CH:10]=[C:11]([O:12][CH3:13])[C:2]([C:21]2[CH:20]=[C:19]3[C:24](=[CH:23][CH:22]=2)[N:16]([CH3:15])[N:17]=[CH:18]3)=[CH:3][C:4]=1[CH2:5][CH2:6][C:7]([OH:14])=[O:29]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 225589101-Methyl-1H-indazole-5-boronic acidHCID 668766776-Bromo-7-methoxychroman-2-one

生成物 1

HCID 444627473-(2-hydroxy-4-methoxy-5-(1-methyl-1H-indazol-5-yl)phenyl)propanoic acid収率 61.9%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒2 回HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

A solution of Intermediate 3 (4.2 g) in dimethoxyethane (50 ml) was added with 1-methyl-1H-indazol-5-ylboronic acid (rgt1, 4.3 g), potassium carbonate (4.5 g), water (50 ml), and tetrakistriphenylphosphinepalladium(0) [henceforth abbreviated as Pd(PPh3)4] (2.7 g, Nacarai), and stirred at 90° C. for 14 hours. This reaction mixture was added with 2 N aqueous sodium hydroxide (5 ml), and further stirred at 80° C. for 0.5 hour. The reaction mixture was added with 1 N aqueous hydrochloric acid (10 ml), and extracted with diethyl ether (30 ml×2), and then the aqueous layer was neutralized with 5 N aqueous hydrochloric acid, and extracted with ethyl acetate. The reaction mixture was washed with saturated aqueous sodium hydrogencarbonate, the organic layer was dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (3.3 g).

後処理

  1. stirringfurther stirred at 80° C. for 0.5 hour
  2. extractionextracted with diethyl ether (30 ml×2)
  3. extractionextracted with ethyl acetate
  4. washThe reaction mixture was washed with saturated aqueous sodium hydrogencarbonate
  5. customthe organic layer was dried
  6. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-66ffef2649ea4307b767647faf75e272
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08334314B2

反応ノート

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