N,N,N',N'-Tetramethylazodicarboxamide → 2-{[1-(Phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine

HRID 2423174Notes

Reaction equation

[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N(C(N(C)C)=O)=NC(N(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:52][CH2:53][NH:54]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:52][CH2:53][NH2:54])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To 1-(phenylsulfonyl)-1 H-indol-5-ol, (Intermediate 8, 8.0 g, 29 mmol) were 1,1′-azobis(N,N-dimethylformamide) (7.6 g, 44 mmol), triphenylphosphine (15.4 g, 580 mmol), tert-butyl N-(2-hydroxy-ethyl)carbamate (9.4 g, 58 mmol) and DCM (200 mL) added. The reaction mixture was heated at 50° C. for 1.5 hours. The reaction mixture was allowed to cool to room temperature and TFA (50 mL) was added. The reaction mixture was stirred for 3 hours and evaporated. The crude material was purified with flash chromatography on silica gel (DCM:MeOH, 95:5) to give the title compound (9.6 g). MS m/z 317 [M+H]+.

Workup

additionadded
temperatureto cool to room temperature
customevaporated
customThe crude material was purified with flash chromatography on silica gel (DCM:MeOH, 95:5)

Sources & evidence

ORD record: ord-b2ad4207de064c29b7fc31c82f8d9cca
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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