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

HRID 2189881ノート

反応式

HRID 2189881 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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), Pd2dba3 (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.

後処理

  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)

出典と根拠

ORDレコード
ord-ebae0cafc95940d2941f2a2f428e7334
出典データセット
uspto-grants-2012_12
特許番号
US08324252B2

反応ノート

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