Iodine → HCID 67157927, compound

HRID 549084Notes

Reaction equation

HRID 549084 reaction equation
[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]

Participants

8

Reactant 5

HCID 807IodineHCID 14797Potassium HydroxideHCID 17051Indole, 6-(benzyloxy)-5-methoxy-HCID 24437Sodium SulfiteHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 67157927HCID 67157927, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent3×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-5311cfaa22cf43819e76d79e4cd36aac
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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