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Sodium Carbonate → N-(3-(2-Methoxybenzyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

HRID 392446
ノート
印刷プレビュー

反応式

HRID 392446 の反応式
Br[CH2:2][C:3]1[CH:4]=[C:5]([N:9]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:2][C:3]1[CH:4]=[C:5]([N:9]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1
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

6

反応物 3

HCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 23521695N-(3-bromomethylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine

生成物 1

HCID 23521678N-(3-(2-Methoxybenzyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium
触媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
50 °C

実験手順

The flask was charged with N-(3-bromomethylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.180 g, 0.500 mmol), 2-methoxyphenylboronic acid (0.113 g, 0.75 mmol), 4.5 ml of DME, 1.5 ml of 2 M Na2CO3, and terakis(triphenylphosphine) palladium(0) (0.018 g, 0.016 mmol). After N2-flushing, the mixture was heated at 50° C. overnight. The reaction mixture was concentrated, diluted with water, and extracted with EtOAc. The organic layer was washed with brine and concentrated. The residue was chromatographed on a silica-gel column with 1:1 to 1:3 toluene/EtOAc to afford the title compound. 1H NMR:, 8.37 (d,1H,J=3.9 Hz), 8.24 (s,1H), 7.55 (d,1H,J=7.8 Hz), 6.74-7.17 (m,9H), 4.76 (s,2H), 3.80 (s,2H), 3.69 (s,2H), 2.94 (q,2H,J=7.3 Hz), 1.32 (t,3H,J=7.3 Hz). MS calcd. 396.2; MS (M+1) 397.2.

後処理

  1. customAfter N2-flushing
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica-gel column with 1:1 to 1:3 toluene/EtOAc

出典と根拠

ORDレコード
ord-3eff67a610a14024858f68e130218ea1
出典データセット
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06800651B2

反応ノート

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