Triethylamine → 2-Fluoro-6-(5-methoxy-benzofuran-2-yl)-pyridin-3-ylamine

HRID 501053

反応式

HRID 501053 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[N:21]=[C:20]([F:22])[C:19]([NH2:23])=[CH:18][CH:17]=1.CCN(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>[F:22][C:20]1[C:19]([NH2:23])=[CH:18][CH:17]=[C:16]([C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][C:7]=3[CH:8]=2)[N:21]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 22221596(5-Methoxy-1-benzofuran-2-yl)boronic acidHCID 594247976-Bromo-2-fluoropyridin-3-amine

生成物 1

HCID 250150202-Fluoro-6-(5-methoxy-benzofuran-2-yl)-pyridin-3-ylamine収率 69.2%

試薬・触媒・溶媒 2

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

反応条件

温度
140 °C

実験手順

5-Methoxybenzofuran boronic acid (345 mg, 1.80 mmol), 6-bromo-2-fluoro-pyridin-3-ylamine (286.5 mg, 1.50 mmol), Pd(PPh3)2Cl2 (25.2 mg, 0.036 mmol) and Et3N (475.5 μL, 3.41 mmol) were mixed in EtOH (10 mL) in a microwave vial. The reaction mixture was stirred at 140° C. for 10 minutes in a microwave reactor. The volatiles were then removed under reduced pressure and water was added (20 mL). The product was extracted with ethyl acetate (30 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. Purification of the crude product by flash column chromatography using 25% ethyl acetate in hexane gave 2-fluoro-6-(5-methoxy-benzofuran-2-yl)-pyridin-3-ylamine (268 mg) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ: 7.58 (d, J=7.6 Hz, 1 H), 7.39 (d, J=9.0 Hz, 1H), 7.15 (m, 1H), 7.14 (s, 1H), 7.04 (d, J=2.6 Hz, 1H), 6.88 (m, 1H), 3.95 (s, 2H), 3.85 (s, 3H). ESMS: m/z 259.47 [M+1]+

後処理

  1. customThe volatiles were then removed under reduced pressure and water
  2. additionwas added (20 mL)
  3. extractionThe product was extracted with ethyl acetate (30 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude product by flash column chromatography

出典と根拠

ORDレコード
ord-b61a99674c7c4908a465ba3c7d3591fc
出典データセット
uspto-grants-2010_08
特許番号
US07772256B2

関連ノート

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