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

HRID 1404092노트

반응식

HRID 1404092 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-f4d3c79341bf4e27ab4bea91d571ed04
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912220B2

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