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1,2-Dimethoxyethane → Ethyl 6-[2-(tert-butoxycarbonylaminomethyl)phenyl]pyridine-2-carboxylate

HRID 395356
ノート
印刷プレビュー

反応式

HRID 395356 の反応式
COCCOC.Br[C:8]1[N:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[CH:10][CH:9]=1.[C:19]([O:23][C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.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>[C:19]([O:23][C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:8]1[N:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[CH:10][CH:9]=1)=[O:25])([CH3:22])([CH3:20])[CH3:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2758810Ethyl 6-BromopicolinateHCID 10911965(2-(((tert-Butoxycarbonyl)amino)methyl)phenyl)boronic acid

生成物 1

HCID 22345551Ethyl 6-[2-(tert-butoxycarbonylaminomethyl)phenyl]pyridine-2-carboxylate収率 72%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 6344Dichloromethane溶媒

実験手順

83 ml of 1,2-dimethoxyethane were aerated with argon, and 481 mg (0.41 mmol) of Pd(PPh3)4 and 1.9 g (8.3 mmol) of ethyl 6-bromopicolinate were added. After 10 min, 3.16 g (12.5 mmol) of 2-(tert-butoxycarbonylaminomethyl)phenylboronic acid and finally 8.3 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux under argon for 18 h, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 2.12 g (72%) of a viscous orange oil were obtained.

後処理

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureto reflux under argon for 18 h
  4. temperatureafter cooling
  5. washwashed with water
  6. customThe organic phase was dried
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel

出典と根拠

ORDレコード
ord-4891c758d3744acea9f210cf9f6c0ba0
出典データセット
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06605625B2

反応ノート

読み込み中…

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