Formaldehyde → 4-{[(2-Hydroxyethyl)(methyl)amino]methyl}-6-methoxy-1-(phenylsulfonyl)-1H-indol-5-ol

HRID 2423133Notes

Reaction equation

[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[CH2:6]=O.[CH3:8][O:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[CH:15][N:16]2[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:12][C:11]=1[OH:28]>CCO>[OH:5][CH2:4][CH2:3][N:2]([CH2:6][C:12]1[C:11]([OH:28])=[C:10]([O:9][CH3:8])[CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][N:16]2[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH3:1]

Participants

Conditions

Temperature: 65 °C

Procedure

To 2-(methylamino)ethanol (0.37 g, 4.9 mmol) and paraformaldehyde (0.15 g, 4.9 mmol) was ethanol (5 mL) added. The reaction mixture was heated at 65° C. for 5 minutes and a clear solution was formed. 6-methoxy-1-(phenylsulfonyl)-1H-indol-5-ol (Intermediate 15, 0.75 g, 2.5 mmol) in EtOH (10 mL) was added in one portion. The mixture was stirred for 2 hours at 70° C. The solvent was removed under reduced pressure and the crude material was dissolved in DCM and was washed with brine. The organic layer was collected and dried (MgSO4) to give the title compound (400 mg). MS m/z 391 [M+H]+.

Workup

additionadded
customa clear solution was formed
customThe solvent was removed under reduced pressure
dissolutionthe crude material was dissolved in DCM
washwas washed with brine
customThe organic layer was collected
dry with materialdried (MgSO4)

Sources & evidence

ORD record: ord-9e389fb9d99e4de28d29265d6c26cb92
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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