N,N,N',N'-Tetramethylazodicarboxamide → 6-Methoxy-2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

HRID 2423134Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]([CH2:6][C:7]1[C:15](O)=[C:14]([O:17][CH3:18])[CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N(C)C)=O)=NC(N(C)C)=O>C1COCC1>[CH3:18][O:17][C:14]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[C:7]2[CH2:6][N:4]([CH3:5])[CH2:3][CH2:2][O:1][C:15]=12

Participants

Conditions

Temperature: 150 °C

Procedure

THF (15 mL) was added to a pyrex tube charged with 4-{[(2-hydroxyethyl)(methyl)amino]methyl}-6-methoxy-1-(phenylsulfonyl)-1H-indol-5-ol (Intermediate 16, 1.02 mmol, 400 mg), triphenylphosphine (2.05 mmol, 537 mg) and 1,1′-azobis(N,N-dimethylformamide) (2.05 mmol, 353 mg). The reaction mixture was heated at 150° C. for 90 minutes in a microwave heater. The crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (137 mg). MS m/z 373 [M+H]+.

Workup

customThe crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN)

Sources & evidence

ORD record: ord-1b365466b93b4bb98f7360eb8d2197db
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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