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Potassium Carbonate → 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(3-methoxyphenyl)-1-(phenylsulfonyl)-

HRID 79531
ノート
印刷プレビュー

反応式

HRID 79531 の反応式
Br[C:2]1[C:3]([Cl:20])=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>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>[Cl:20][C:3]1[C:2]([C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([O:22][CH3:21])[CH:28]=2)=[CH:7][N:6]=[C:5]2[N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:4]=12
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 11430Potassium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 497588851H-Pyrrolo[2,3-B]pyridine, 5-bromo-4-chloro-1-(phenylsulfonyl)-

生成物 1

HCID 687603871H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(3-methoxyphenyl)-1-(phenylsulfonyl)-収率 76.1%

試薬・触媒・溶媒 1

HCID 178418397
HCID 178418397、化合物
触媒

反応条件

温度
80 °C

実験手順

5-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyri dine (0.750 g, 2.01 mmol, see Example 6), 3-methoxyphenylboronic acid (0.321 g, 2.11 mmol), Pd(PPh3)4 (0.116 g, 0.100 mmol) and K2CO3 (4.20 mL, 3.02 mmol) were added to an Ar degassed solution of 2:1 toluene:EtOH (8 mL). The reaction was then heated to 80° C. overnight. The reaction was then poured into water and extracted with DCM. The organic fractions were dried, filtered, and concentrated to give the crude product. The crude product was purified (1:1 to 1:2 hexane:DCM) to give 4-chloro-5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.610 g, 75.8% yield).

後処理

  1. customdegassed solution of 2:1 toluene
  2. additionThe reaction was then poured into water
  3. extractionextracted with DCM
  4. customThe organic fractions were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customThe crude product was purified (1:1 to 1:2 hexane:DCM)

出典と根拠

ORDレコード
ord-3689acb783464112bd062ca5362ae951
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841304B2

反応ノート

読み込み中…

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