Dimethylformamide dimethyl acetal → 1-[5,6-Dimethoxy-1-(phenylsulfonyl)-1H-indol-4-yl]-N,N-dimethylmethanamine

HRID 1159865Notes

Reaction equation

HRID 1159865 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:13]([OH:14])=[C:12]([O:15][CH3:16])[CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH3:3].[CH3:26]N(C(OC)OC)C>CN(C=O)C>[CH3:26][O:14][C:13]1[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])=[C:6]2[C:10](=[CH:11][C:12]=1[O:15][CH3:16])[N:9]([S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:18])=[O:19])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 595135364-[(Dimethylamino)methyl]-6-methoxy-1-(phenylsulfonyl)-1H-indol-5-ol

Product 1

HCID 595135671-[5,6-Dimethoxy-1-(phenylsulfonyl)-1H-indol-4-yl]-N,N-dimethylmethanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[(Dimethylamino)methyl]-6-methoxy-1-(phenylsulfonyl)-1H-indol-5-ol (60 mg, 0.166 mmol; Example 184) was dissolved in DMF (2 ml) and DMF-DMA (300 μl) was added. The mixture was heated in microwave oven at 180 oC for 180 s. Solvent was evaporated and the residue purified on Gilson HPLC using 30-60% MeCN in 50 nM ammonium hydrogencarbonate buffer as eluent. Yield: 13.2 mg (21%); brown oil. MS (ESI+) for C19H22N2O4S m/z 375 (M+H)+.

Workup

  1. temperatureThe mixture was heated in microwave oven at 180 oC for 180 s
  2. customSolvent was evaporated
  3. customthe residue purified on Gilson HPLC

Sources & evidence

ORD record
ord-9c8d96670a1f45fe91c2de5ea59b17df
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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