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Triethylamine → 5-(5-methoxy-1-benzofuran-2-yl)-N-methyl-2-pyridinamine

HRID 501045
ノート
印刷プレビュー

反応式

HRID 501045 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](B(O)O)=[CH:8][C:7]=2[CH:14]=1.Br[C:16]1[CH:17]=[CH:18][C:19](CN)=[N:20][CH:21]=1.C[CH2:25][N:26](CC)CC>CCO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:16]3[CH:17]=[CH:18][C:19]([NH:26][CH3:25])=[N:20][CH:21]=3)=[CH:8][C:7]=2[CH:14]=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 8471TriethylamineHCID 22221596(5-Methoxy-1-benzofuran-2-yl)boronic acidHCID 49761678(5-Bromopyridin-2-yl)methanamine

生成物 1

HCID 250149275-(5-methoxy-1-benzofuran-2-yl)-N-methyl-2-pyridinamine

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 702
Ethanol
溶媒

反応条件

温度
140 °C

実験手順

5-methoxybenzofuran boronic acid (1.2 mmol), 5-bromopyridine-2-methylamine (1.0 mmol), Pd(PPh3)2Cl2 (0.024 mmol) and NEt3 (317 μL) were mixed in EtOH (10 mL) in a 20 mL microwave vial. The mixture was stirred at 140° C. for 10 min in a microwave reactor. The solvent was removed under vacuum, water was added and the solution was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude substance was purified by preparative HPLC to afford the title compound as a white solid (100 mg). 1H NMR δ ppm 8.53 (d, 1 H) 7.84 (dd, 1 H) 7.44 (d, 1 H) 7.08 (d, 1 H) 7.04 (s, 1 H) 6.91 (d, 1 H) 6.81 (dd, 1 H) 6.55 (d, 1 H) 3.78 (s, 3 H) 2.83 (d, 3 H); MS m/z 255 (M+H).

後処理

  1. customThe solvent was removed under vacuum, water
  2. additionwas added
  3. extractionthe solution was extracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude substance was purified by preparative HPLC

出典と根拠

ORDレコード
ord-8ad2f55ea3354d9d9658c58ecd140d4a
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07772256B2

反応ノート

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