Iodine → HCID 67157927, 화합물

HRID 549084노트

반응식

HRID 549084 반응식
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[I:22]I.[C:24]([O:28][C:29]([O:31]C(OC(C)(C)C)=O)=O)([CH3:27])([CH3:26])[CH3:25].S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:24]([O:28][C:29]([N:15]1[C:16]2[C:12](=[CH:11][C:10]([O:18][CH3:19])=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:17]=2)[C:13]([I:22])=[CH:14]1)=[O:31])([CH3:27])([CH3:26])[CH3:25]

참가 물질

8

반응물 5

HCID 807IodineHCID 14797Potassium HydroxideHCID 170516-Benzyloxy-5-methoxyindoleHCID 24437Sodium SulfiteHCID 90495Di-tert-butyl dicarbonate

생성물 1

HCID 67157927HCID 67157927, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매3회

실험 절차

A solution of 6-benzyloxy-5-methoxyindole (1.90 g, prepared according to procedure described by Benigni, J. D. and Minnis, R. L., J. Heterocycl. Chem. 1965, 2, 387 and Sinhababu, A. K. and Borchardt, R. T., J. Org. Chem. 1983, 48, 3347) in dry dimethylformamide (37.5 mL) was treated with ground potassium hydroxide (1.24 g) and a solution of iodine (1.96 g) in dry dimethylformamide (37.5 mL) dropwise at room temperature. The reaction mixture was stirred at room temperature for 2 hours, then treated with 4-dimethylaminopyridine (69 mg) followed by a solution of di-tert-butyldicarbonate (2.05 g) in dry dimethylformamide and stirring was continued for a further 1 hour. The reaction mixture was poured into aqueous sodium sulfite solution (0.2%). The aqueous phase was extracted three times with ethyl acetate (100 mL). The combined organic phases were washed with water (100 mL), then with brine (100 mL), then dried over magnesium sulfate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of cyclohexane and ethyl acetate (1:9, v/v) to give the title compound (3.35 g) as a white solid. TLC: RF=0.58 (dichloromethane). MS: EI (70 eV); m/z=479 M+. (45%); 423 (100%); 332 (75%).

후처리

  1. customdropwise at room temperature
  2. stirringstirring
  3. waitwas continued for a further 1 hour
  4. extractionThe aqueous phase was extracted three times with ethyl acetate (100 mL)
  5. washThe combined organic phases were washed with water (100 mL)
  6. dry with materialwith brine (100 mL), then dried over magnesium sulfate
  7. customevaporated
  8. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of cyclohexane and ethyl acetate (1:9, v/v)

출처 및 근거

ORD 기록
ord-5311cfaa22cf43819e76d79e4cd36aac
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943616B2

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