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

HRID 501053

반응식

HRID 501053 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 702Ethanol용매

반응 조건

온도
140 °C

실험 절차

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]+

후처리

  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

출처 및 근거

ORD 기록
ord-b61a99674c7c4908a465ba3c7d3591fc
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772256B2

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