Cesium carbonate → (2-Chloro-pyridin-4-yl)-(5-cyclopropyl-1H-pyrazole-3-yl)-amine

HRID 75921노트

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HRID 75921 반응식
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.C(OC([N:16]1[C:20]([CH:21]2[CH2:23][CH2:22]2)=[CH:19][C:18]([NH2:24])=[N:17]1)=O)(C)(C)C.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.C([O-])([O-])=O.[Cs+].[Cs+]>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]>[Cl:8][C:4]1[CH:3]=[C:2]([NH:24][C:18]2[CH:19]=[C:20]([CH:21]3[CH2:23][CH2:22]3)[NH:16][N:17]=2)[CH:7]=[CH:6][N:5]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 15165112-Chloro-4-iodopyridineHCID 11218347tert-butyl 3-amino-5-cyclopropyl-1H-pyrazole-1-carboxylate

생성물 1

HCID 86620618(2-Chloro-pyridin-4-yl)-(5-cyclopropyl-1H-pyrazole-3-yl)-amine수율 48%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

A mixture of 4-iodo-2-chloropyridine (0.26 g, 1.1 mmol), 3-amino-5-cyclopropyl-pyrazole-1-carboxylic acid tert-butyl ester (0.20 g, 0.89 mmol), Pd2 dba3 (0.016 g, 2 mol %), Xantphos (0.031 g, 6 mol %), and Cs2CO3 (0.41 g, 1.3 mmol) in degassed toluene (4 ml) was purged with N2 and heated to 100° C. in a sealed tube for 2 days. The mixture was diluted with THF and filtered to remove Cs2CO3. The filtrate was concentrated under reduced pressure and purified by column chromatography (hexane-EtOAc=3:1) to give the title compound (0.10 g, 48%). MS: Calcd.: 234. Found: [M+H]+ 235.

후처리

  1. customwas purged with N2
  2. additionThe mixture was diluted with THF
  3. filtrationfiltered
  4. customto remove Cs2CO3
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by column chromatography (hexane-EtOAc=3:1)

출처 및 근거

ORD 기록
ord-003cbea543f74ba8aa8ddb5f0d572428
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835465B2

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