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

HRID 1072607

反応式

HRID 1072607 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 74236Tetrabutylammonium Bromide触媒HCID 1049Pyridine溶媒HCID 1140Toluene溶媒2 回HCID 14798Sodium Hydroxide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c496902e20ac473d8baa4a21b4e14b25
出典データセット
uspto-grants-2005_06
特許番号
US06911463B2

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