Water → 2-(7-fluoro-4-methoxy-1-methyl-5-phenyl-1H-indol-3-yl)-N,N-dimethylacetamide

HRID 1404092ノート

反応式

HRID 1404092 の反応式
Br[C:2]1[C:3]([O:19][CH3:20])=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH3:12])[CH:6]=[C:5]2[CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:11][C:9]1[CH:10]=[C:2]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]([O:19][CH3:20])=[C:4]2[C:8]=1[N:7]([CH3:12])[CH:6]=[C:5]2[CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15]

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 669270242-(5-bromo-7-fluoro-4-methoxy-1-methyl-1H-indol-3-yl)-N,N-dimethylacetamide

生成物 1

HCID 669270952-(7-fluoro-4-methoxy-1-methyl-5-phenyl-1H-indol-3-yl)-N,N-dimethylacetamide収率 81%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

To the solution of 8-11 (200 mg, 0.58 mmol) in dioxane (10 mL) was added phenylboronic acid (86 mg, 0.70 mmol), Pd(PPh3)4 (68 mg, 0.06 mmol), and Cs2CO3 (760 mg, 2.3 mmol) under nitrogen atmosphere. The reaction mixture was refluxed overnight, poured into water and extracted with ethyl acetate (20 mL×3). The separated organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (elution with petroleum ether:ethyl acetate=1:1) to afford 8-12 (160 mg, 81%) as white solid. LCMS: calc 340.4 and found 341.1 [MH]+.

後処理

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionextracted with ethyl acetate (20 mL×3)
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (elution with petroleum ether:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-f4d3c79341bf4e27ab4bea91d571ed04
出典データセット
uspto-grants-2014_12
特許番号
US08912220B2

反応ノート

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