ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Sodium Carbonate → cyclopropanecarboxylic acid [4-bromo-3-(2-methyl-2H-indazol-5-yl)-isothiazol-5-yl]-amide

HRID 2079748
ノート
印刷プレビュー

反応式

HRID 2079748 の反応式
Br[C:2]1[C:6]([Br:7])=[C:5]([NH:8][C:9]([CH:11]2[CH2:13][CH2:12]2)=[O:10])[S:4][N:3]=1.[CH3:14][N:15]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20](B3OC(C)(C)C(C)(C)O3)=[CH:21]2)=[N:16]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Cl-].[Na+].O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:7][C:6]1[C:2]([C:20]2[CH:19]=[CH:18][C:17]3[C:22](=[CH:23][N:15]([CH3:14])[N:16]=3)[CH:21]=2)=[N:3][S:4][C:5]=1[NH:8][C:9]([CH:11]1[CH2:13][CH2:12]1)=[O:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 441182532-Methyl-2H-indazole-5-boronic acid, pinacol esterHCID 66838483Cyclopropanecarboxylic acid (3,4-dibromo-isothiazol-5-yl)-amide

生成物 1

HCID 66838434cyclopropanecarboxylic acid [4-bromo-3-(2-methyl-2H-indazol-5-yl)-isothiazol-5-yl]-amide収率 50%

試薬・触媒・溶媒 4

HCID 178418476
HCID 178418476、化合物
触媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒
HCID 57417360Sodium chloride; water溶媒

実験手順

Degas by bubbling nitrogen for 10; min through a mixture of cyclopropanecarboxylic acid (3,4-dibromo-isothiazol-5-yl)-amide (1.04; g, 3.19; mmol) and 2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2H-indazole (1.29; g, 3.51 mmol) in 1,4-dioxane (16; mL) and a 2M aqueous solution of sodium carbonate (7.98 mL). Add bis(triphenylphosphine)palladium(II) chloride (448; mg, 0.64; mmol) and heat at 80° C. for 12; h. Cool, dilute with brine and ethyl acetate and separate the layers. Extract the aqueous phase twice with ethyl acetate. Dry the combined organic phases over sodium sulfate, filter, concentrate and purify by silica gel chromatography, gradient eluting from 40:60; to 100:0; using ethyl acetate:hexanes, to give the title compound as a solid (0.6; g, 1.59; mmol, 50%). MS (m/z): 377, 379; (M+1).

後処理

  1. customDegas
  2. customby bubbling nitrogen for 10
  3. temperatureCool
  4. customseparate the layers
  5. extractionExtract the aqueous phase twice with ethyl acetate
  6. dry with materialDry the combined organic phases over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. custompurify by silica gel chromatography
  10. washgradient eluting from 40:60

出典と根拠

ORDレコード
ord-6a52857fbb7d40d69a62b36f8c904910
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932274B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート