Dichloromethane → 5,7-Difluoro-3-iodo-1-(phenylsulfonyl)-1H-indole

HRID 1072607

반응식

HRID 1072607 반응식
[I:1]Cl.C(Cl)Cl.[F:6][C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([F:16])[CH:15]=1)[NH:12][CH:11]=[CH:10]2.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1.C1(C)C=CC=CC=1.[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:17]1([S:23]([N:12]2[C:13]3[C:9](=[CH:8][C:7]([F:6])=[CH:15][C:14]=3[F:16])[C:10]([I:1])=[CH:11]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

9

반응물 4

HCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 24640Iodine chlorideHCID 27787305,7-difluoro-1H-indole

생성물 1

HCID 220147845,7-Difluoro-3-iodo-1-(phenylsulfonyl)-1H-indole수율 87%

시약·촉매·용매 4

HCID 74236Tetrabutylammonium Bromide촉매HCID 1049Pyridine용매HCID 1140Toluene용매2회HCID 14798Sodium Hydroxide용매

실험 절차

The 1.0 M ICl in CH2Cl2 (43 ml, 43 mmol) is added to a solution of 5,7-difluoro-indole (6 g, 39 mmol) in 35 ml pyridine under N2 at 0° C. and the resulting mixture is stirred for 30 minutes. The reaction is diluted with toluene and washed with brine, 1N HCl, 1N NaOH, dried (Na2SO4), filtered and concentrated. The crude 3-iodo-5,7-difluoroindole is stirred in toluene (85 ml) and 5 N NaOH (70 ml), tetrabutylammonium bromide (1.25 g, 3.9 mmol), then benzenesulfonyl chloride (6.2 ml, 48 mmol) are added and the resulting mixture is stirred 24 hours. The two phase reaction mixture is diluted with toluene, washed with brine, dried(Na2SO4), filtered, concentrated and the residue is triturated with diethyl ether/petroleum ether. The resulting solid is filtered to give 14.2 g of N-Benzenesulfonyl-3-iodo-5,7-difluoroindole (87%).

후처리

  1. washwashed with brine, 1N HCl, 1N NaOH
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. stirringThe crude 3-iodo-5,7-difluoroindole is stirred in toluene (85 ml)
  6. stirringthe resulting mixture is stirred 24 hours
  7. customThe two phase reaction mixture
  8. washwashed with brine, dried(Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customthe residue is triturated with diethyl ether/petroleum ether
  12. filtrationThe resulting solid is filtered

출처 및 근거

ORD 기록
ord-c496902e20ac473d8baa4a21b4e14b25
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06911463B2

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