Sodium Carbonate → HCID 66728062、化合物

HRID 573265ノート

反応式

HRID 573265 の反応式
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([CH3:11])[CH:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([O-:14])=[O:13].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.CCOC(C)=O.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>[CH3:11][N:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:2]([C:18]2[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)=[CH:3]1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 667278953-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine

生成物 1

HCID 66728062HCID 66728062、化合物収率 37.1%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine (200 mg), (4-nitrophenyl)boronic acid (175 mg), Pd(PPh3)4 (95 mg) and Na2CO3 (201 mg) in DME (4 mL) and water (2 mL) was heated at 100° C. for 19 h. After this time, the reaction was cooled to room temperature, diluted with AcOEt (100 mL), washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (heptane to 1:1 AcOEt/heptane) to give the title compound (89 mg).

後処理

  1. temperatureAfter this time, the reaction was cooled to room temperature
  2. washwashed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by silica gel column chromatography (heptane to 1:1 AcOEt/heptane)

出典と根拠

ORDレコード
ord-9dc8ae946d9746adbd26d72514820ecf
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

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