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Tetrahydrofuran → N-[5-(6-cyclopentylimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-dimethyl-propanamide

HRID 539749
ノート
印刷プレビュー

反応式

HRID 539749 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:24]([F:27])([F:26])[F:25])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=3)=[CH:10][N:4]2[N:3]=1.[Br-].[CH:29]1([Zn+])[CH2:31][CH2:30]1.[CH2:33]1COC[CH2:34]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:30]1([C:2]2[CH:7]=[CH:6][C:5]3=[N:8][C:9]([C:11]4[CH:12]=[CH:13][C:14]([C:24]([F:27])([F:26])[F:25])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=4)=[CH:10][N:4]3[N:3]=2)[CH2:31][CH2:29][CH2:34][CH2:33]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 86667850N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-(trifluoromethyl)phenyl)pivalamideHCID 178419765HCID 178419765、化合物

生成物 1

HCID 67983831N-[5-(6-cyclopentylimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-dimethyl-propanamide収率 11%

試薬・触媒・溶媒 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒

反応条件

温度
150 °C

実験手順

A small vial is charged with N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide (0.032 g, 0.08 mol), cyclopropylzinc bromide (0.12 mL, 2 M in THF, 0.24 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (6 mg, 0.01 mol), and THF (0.32 mL). The reaction vessel is purged with N2 and heated to 150° C. in the microwave for 2 hr. Sat. aqueous NH4Cl is added to the mixture and it is extracted with EtOAc. The combined organic layers are dried over Na2SO4, filtered, concentrated, and purified by silica gel chromatography (hexanes to ethyl acetate) to give the title compound (3.5 mg, 11% yield). LCMS m/z=431.5 [M+H]+, tR=3.21 min. (compound same as Example 316)

後処理

  1. customThe reaction vessel is purged with N2
  2. additionSat. aqueous NH4Cl is added to the mixture and it
  3. extractionis extracted with EtOAc
  4. dry with materialThe combined organic layers are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (hexanes to ethyl acetate)

出典と根拠

ORDレコード
ord-d11ab9d574bf460cb8840eda05612d6a
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08871767B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート