1H-Pyrazole, 4-chloro- → HCID 90415524、化合物

HRID 578850ノート

反応式

HRID 578850 の反応式
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9](Br)[C:10]([O:13][CH:14](F)F)=[N:11][CH:12]=2)[CH:5]=[N:4][CH:3]=[N:2]1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.[Cl:52][C:53]1[CH:54]=[N:55][NH:56][CH:57]=1>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]>[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([N:55]3[CH:54]=[C:53]([Cl:52])[CH:57]=[N:56]3)[C:10]([O:13][CH3:14])=[N:11][CH:12]=2)[CH:5]=[N:4][CH:3]=[N:2]1

参加物

7

反応物 4

HCID 275241H-Pyrazole, 4-chloro-HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 90414984HCID 90414984、化合物2 回

生成物 1

HCID 90415524HCID 90415524、化合物収率 46.5%

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

To a solution of 5-((1H-1,2,4-triazol-1-yl)methyl)-3-Bromo-2-methoxypyridine (Intermediate 13), (100 mg, 0.37 mmol), in toluene (5 mL) was added tris(dibenzylideneacetone)dipalladium(0) (34.1 mg, 0.04 mmol), sodium tert-butoxide (71.6 mg, 0.74 mmol), (2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (29.3 mgs, 0.07 mmol) and 4-chloro-1H-pyrazole (37.3 mg, 0.37 mmol). The mixture was heated at 100° C. for 30 min. The mixture was quenched with water (0.5 mL), diluted with ethyl acetate (10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. Purification (FCC, SiO2, 20-100% EtOAc/hexanes) afforded the title compound (50 mg, 46%). 1H NMR (400 MHz, DMSO-d6) δ 8.69 (s, 1H), 8.07 (s, 2H), 8.01 (q, J=2.3 Hz, 2H), 7.99 (s, 1H), 5.37 (s, 2H), 3.94 (s, 3H), 2.52 (s, 1H). [M+H]=292.12.

後処理

  1. customThe mixture was quenched with water (0.5 mL)
  2. additiondiluted with ethyl acetate (10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification (FCC, SiO2, 20-100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-cea5b33739754b4e98db49361842ff56
出典データセット
uspto-grants-2015_05
特許番号
US09040692B2

反応ノート

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