Sodium Bicarbonate → 2-Aminocarbonylamino-6-(4-hydroxymethylpyridin-2-yl)indole-3-carboxamide

HRID 216627ノート

反応式

HRID 216627 の反応式
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14](=[O:16])[NH2:15])=[CH:11][CH:10]=[C:9](B1OC(C)(C)C(C)(C)O1)[CH:8]=2)=[O:3].C(=O)([O-])O.[Na+].Br[C:32]1[CH:37]=[C:36]([CH2:38][OH:39])[CH:35]=[CH:34][N:33]=1>O.O1CCOCC1.[Cl-].[Na+].O.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>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14]([NH2:15])=[O:16])=[CH:11][CH:10]=[C:9]([C:32]1[CH:37]=[C:36]([CH2:38][OH:39])[CH:35]=[CH:34][N:33]=1)[CH:8]=2)=[O:3]

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 14512957(2-Bromopyridin-4-yl)methanolHCID 591897502-Aminocarbonylamino-3-carbamoylindole-6-boronic acid pinacol ester2 回

生成物 1

HCID 591899142-Aminocarbonylamino-6-(4-hydroxymethylpyridin-2-yl)indole-3-carboxamide収率 23.6%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 218864351,4-Dioxane--water (1/1)溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

A solution mixture of 2-aminocarbonylamino-3-carbamoylindole-6-boronic acid pinacol ester (Compound 6-1, 90 mg, 0.26 mmol), sodium hydrogen carbonate (55 mg, 0.65 mmol), 2-bromopyridine-4-methanol (58 mg, 0.31 mmol) and tetrakis(triphenylphosphine)palladium (0) (15 mg, 0.013 mmol) in water-1,4-dioxane (1:3, 15 mL) was stirred at 100° C. for 6 hours. Brine (5 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (5 mL). The organic layer was dried over anhydrous magnesium sulfate, and was filtered throught Celite® pad. After the solvent was evaporated under reduced pressure, the resultant solid was washed with ethanol (2 mL), and dried under reduced pressure to give the title compound (20 mg) as a brown solid (yield 23%).

後処理

  1. extractionthe whole was extracted with ethyl acetate (5 mL)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationwas filtered
  4. customAfter the solvent was evaporated under reduced pressure
  5. washthe resultant solid was washed with ethanol (2 mL)
  6. customdried under reduced pressure

出典と根拠

ORDレコード
ord-254dc5bafe4a48ddaa493831133fd402
出典データセット
uspto-grants-2012_06
特許番号
US08193237B2

反応ノート

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