2,6-Lutidine → 1-Tosyl-1H-indole-4-carbaldehyde

HRID 1159754

반응식

HRID 1159754 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[C:15]([CH:20]=C)[CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:31].[Na+]>O1CCOCC1.O.O=[Os](=O)(=O)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=[O:31])[C:14]=3[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 79372,6-LutidineHCID 124465911-[(4-Methylphenyl)sulfonyl]-4-vinyl-1H-indole2회HCID 23667635Sodium periodate

생성물 1

HCID 131150931-Tosyl-1H-indole-4-carbaldehyde

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

OsO4 (6 mg, 0.023 mmol) was added to a stirred mixture of 1-[(4-methylphenyl)sulfonyl]-4-vinyl-1H-indole (68 mg, 0.23 mmol; Intermediate 4) and 2,6-lutidine (54 μL, 0.46 mmol) in dioxane (6 mL). The mixture turned from colorless to black in 1 minute. Sodium periodate (0.197 g, 0.92 mmol) in water (1.5 mL, warmed to dissolve) was added. A grey precipitation was immediately formed. The mixture was stirred for 20 min. and partitioned between 2M aqueous HCl (25 mL) and DCM (25 mL). The organic layer was dried, filtered and combined with Intermediate 5 batch 2.

후처리

  1. customblack in 1 minute
  2. customA grey precipitation
  3. customwas immediately formed
  4. custompartitioned between 2M aqueous HCl (25 mL) and DCM (25 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-6975bbe82eba42e4a72b4b46ff4c6e5e
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812017B2

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