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Sodium Carbonate Decahydrate → 3-(6-Methoxynaphthalen-2-yl)pyridin-2-amine

HRID 1405787
ノート
印刷プレビュー

反応式

HRID 1405787 の反応式
Br[C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16](B(O)O)[CH:15]=[CH:14]2.O.O.O.O.O.O.O.O.O.O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1)[CH:15]=[CH:14]2
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

7

反応物 3

HCID 151402Sodium Carbonate DecahydrateHCID 8177002-Amino-3-bromopyridineHCID 46416926-Methoxy-2-naphthaleneboronic acid

生成物 1

HCID 655501443-(6-Methoxynaphthalen-2-yl)pyridin-2-amine収率 115.6%

試薬・触媒・溶媒 3

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

反応条件

温度
70 °C

実験手順

Tetrakis(triphenylphosphine)palladium(0) (95 mg) was added to a suspension of 3-bromopyridin-2-amine (713.7 mg), 6-methoxynaphthalen-2-ylboronic acid (1000 mg) and sodium carbonate decahydrate (2361 mg) in DME (15 mL) and water (3 mL) and the mixture was stirred at 80° C. under nitrogen for 3 hr and at 70° C. overnight. Activated carbon was added and the insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc) and the volatiles were removed in vacuo to give the title compound (1194 mg) as a crude orange solid. This product was subjected to the next reaction without further purification.

後処理

  1. additionActivated carbon was added
  2. customthe insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc)
  3. customthe volatiles were removed in vacuo

出典と根拠

ORDレコード
ord-34394939926c4b019ae2340cca11ad75
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08916551B2

反応ノート

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