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

HRID 216627노트

반응식

HRID 216627 반응식
[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]

참가 물질

7

반응물 3

HCID 516892Sodium BicarbonateHCID 14512957(2-Bromopyridin-4-yl)methanolHCID 591897502-Aminocarbonylamino-3-carbamoylindole-6-boronic acid pinacol ester2회

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 218864351,4-Dioxane--water (1/1)용매HCID 57417360Sodium chloride; water용매

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온도
100 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-254dc5bafe4a48ddaa493831133fd402
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193237B2

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