Dimethylamine → 4-[(Dimethylamino)methyl]-6-methoxy-1-(phenylsulfonyl)-1H-indol-5-ol

HRID 1159864Notes

Reaction equation

[CH2:1]=O.[NH:3]([CH3:5])[CH3:4].CO.[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>[CH3:4][N:3]([CH2:1][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])[CH3:5]

Participants

Conditions

Temperature: 80 °C

Procedure

Paraformaldehyde (28 mg, 0.932 mmol) and 2 M Me2NH in MeOH (0.47 ml, 0.932 mmol) was heated until clear solution was obtained. The solution was added to 6-methoxy-1-(phenylsulfonyl)-1H-indol-5-ol (61 mg, 0.201 mmol; Intermediate 101) in EtOH (1.5 ml) and the mixture was heated in microwave oven at 80° C. for 10 min. A small part was purified on Gilson HPLC using 25-55% MeCN in 50 nM ammonium hydrogencarbonate as eluent. Yield: 3.8 mg; white solid. MS (ESI+) for C18H20N2O4S m/z 361 (M+H)+.

Workup

customwas obtained
customA small part was purified on Gilson HPLC

Sources & evidence

ORD record: ord-a6f0345992f5416e97e6c855beac96aa
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812017B2

Reaction notes

Loading…