Cesium carbonate → HCID 71061452、化合物

HRID 2201765

反応式

HRID 2201765 の反応式
Br[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:17]1([C:21]([NH2:23])=[O:22])[CH2:20][CH2:19]C1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[NH:8]1[C:7]2=[C:2]([NH:23][C:21]([CH:17]3[CH2:20][CH2:19]3)=[O:22])[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9]1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 1274476Cyclobutanecarboxamide2 回HCID 196964567-Bromo-6-azaindole

生成物 1

HCID 71061452HCID 71061452、化合物収率 39.3%

試薬・触媒・溶媒 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

To a solution of 7-bromo-1H-pyrrolo[2,3-c]pyridine (500 mg, 2.53 mmol) in toluene were added tris (dibenzylidene acetone)dipalladium (116.20 mg, 0.126 mmol), Xantphos (32.98 mg, 0.057 mmol), cesium carbonate (896 mg, 2.75 mmol), and cyclobutanecarboxamide (251 mg, 2.96 mmol, Intermediate 4). The resulting reaction mixture was heated to 120° C. and stirred for 8 hours. After cooling to room temperature a saturated aqueous sodium bicarbonate solution (20 mL) was added to the reaction mixture and extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography to afford N-(1H-pyrrolo[2,3-c]pyridin-7-yl)cyclopropane carboxamide (200 mg, 36% yield).

後処理

  1. customThe resulting reaction mixture
  2. additionwas added to the reaction mixture
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel (100-200) column chromatography

出典と根拠

ORDレコード
ord-8b25761b28a245c19f0b2472249b7716
出典データセット
uspto-grants-2016_06
特許番号
US09364466B2

関連ノート

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