Water → 1-(Methoxymethyl)-7-nitro-2-(1,3-thiazol-2-yl)-1H-indole

HRID 1851369Notes

Reaction equation

HRID 1851369 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]1[S:16][CH:17]=[CH:18][N:19]=1)=[CH:11]2)([O-:5])=[O:4].[CH3:20][O:21][CH2:22]Cl.O>CN(C)C=O.O1CCCC1>[CH3:20][O:21][CH2:22][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[N+:3]([O-:5])=[O:4])[CH:11]=[C:12]1[C:15]1[S:16][CH:17]=[CH:18][N:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 579018457-Nitro-2-(1,3-thiazol-2-yl)-1H-indole

Product 1

HCID 579018301-(Methoxymethyl)-7-nitro-2-(1,3-thiazol-2-yl)-1H-indoleYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60% in oil, 0.47 g) in N,N-dimethylformamide (15 mL) was slowly added 7-nitro-2-(1,3-thiazol-2-yl)-1H-indole (2.21 g) at 0° C., and the mixture was stirred for 20 min. To the reaction mixture was added a solution of chloromethyl methyl ether (0.81 mL) in tetrahydrofuran (2 mL) at 0° C. over 20 min, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (2.14 g, yield 82%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1c150a54064a44c09bc5c61afcc039c8
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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