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Cesium carbonate → 5-Cyclopropylpyridin-3-amine

HRID 2171242
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HRID 2171242 반응식
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1.O.Br[C:21]1[CH:22]=[C:23]([NH2:27])[CH:24]=[N:25][CH:26]=1>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>[CH:1]1([C:21]2[CH:22]=[C:23]([NH2:27])[CH:24]=[N:25][CH:26]=2)[CH2:3][CH2:2]1
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참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 8176813-Amino-5-bromopyridineHCID 2760897Cyclopropylboronic acidHCID 218864351,4-Dioxane--water (1/1)

생성물 1

HCID 665204195-Cyclopropylpyridin-3-amine수율 81%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매

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온도
100 °C

실험 절차

Cyclopropylboronic acid (360 mg), cesium carbonate (1.4 g), and Pd(PPh3)4 (166 mg) were added to a 1,4-dioxane/water (4.5 ml/0.5 ml) solution containing 5-bromopyridin-3-amine (500 mg) in a nitrogen atmosphere, followed by stirring in a sealed tube at 100° C. for 5 hours. The reaction solution was adjusted to room temperature and water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, and the obtained residue was purified by silica gel chromatography (chloroform:MeOH=1:0 to 30:1). A brown solid of 5-cyclopropyl pyridin-3-amine (314 mg) was thus obtained.

후처리

  1. customwas adjusted to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layers were washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (chloroform:MeOH=1:0 to 30:1)

출처 및 근거

ORD 기록
ord-794a78d0be494970a4d12b919ed4c965
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09051310B2

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