Ethanol → 5-Amino-2-(3-cyano-5-fluoro-benzenesulfonyl)-3-(3-chlorophenyl)-thieno[2,3-b]-pyridine

HRID 2384522노트

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HRID 2384522 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:10](Br)=[C:9]([S:12]([C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([C:22]#[N:23])[CH:16]=3)(=[O:14])=[O:13])[S:8][C:5]2=[N:6][CH:7]=1.C(O)C.[Cl:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[NH2:1][C:2]1[CH:3]=[C:4]2[C:10]([C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:27])[CH:33]=3)=[C:9]([S:12]([C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([C:22]#[N:23])[CH:16]=3)(=[O:14])=[O:13])[S:8][C:5]2=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 68521334HCID 68521334, 화합물

생성물 1

HCID 445465635-Amino-2-(3-cyano-5-fluoro-benzenesulfonyl)-3-(3-chlorophenyl)-thieno[2,3-b]-pyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

5-Amino-3-bromo-2-(3-cyano-5-fluoro-benzenesulfonyl)-thieno[2,3-b]pyridine (1.25 g, 30 mmol) was dissolved in toluene (18 ml) and ethanol (20 ml) under argon atmosphere. To the solution Pd(PPh3)4 (175 mg, 0.15 mmol), 3-chlorophenylboronic acid (0.58 g, 37 mmol) and 2M solution of Na2CO3 (15 ml) was added. The reaction mixture was refluxed for 1 hour then it was filtered through celite and washed with toluene (2×5 ml). The filtrate was tightened in vacuum; water (13 ml) and ethyl acetate (13 ml) were added to the residue. It was separated and the water phase was extracted with ethyl acetate (2×5 ml). The organic phase was washed with water (5.0 ml), dried over Na2SO4, filtered, and concentrated under vacuum. The crude product was purified by column chromatography (Kieselgel 60, ethyl acetate:hexane=2:1) to yield the title compound which was purified by stirring with methanol (5 ml) to give 0.84 g (63%) yellow amorphous material. LC-MS: (M+H)+ 444.2. 1H NMR (400 MHz, DMSO-d6, 25° C.): 5.68 (s, 2H); 6.80 (d, J=2.6 Hz, 1H); 7.13-7.22 (m, 2H); 7.53 (t, J=7.9 Hz, 1H); 7.56-7.65 (m, 3H); 8.24 (dm, J=8.4 Hz, 1H); 8.27 (d, J=2.6 Hz, 1H).

후처리

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. filtrationit was filtered through celite
  3. washwashed with toluene (2×5 ml)
  4. additionwater (13 ml) and ethyl acetate (13 ml) were added to the residue
  5. customIt was separated
  6. extractionthe water phase was extracted with ethyl acetate (2×5 ml)
  7. washThe organic phase was washed with water (5.0 ml)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customThe crude product was purified by column chromatography (Kieselgel 60, ethyl acetate:hexane=2:1)

출처 및 근거

ORD 기록
ord-0c11073d69954db1abac7f9ec14b2ab1
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263773B2

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