Triphenylphosphine → 2-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamine

HRID 1777545Notes

Reaction equation

[N:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=2)[NH:8][C:7]=1[Si](CC)(CC)CC)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO>[F:17][C:15]([F:16])([F:18])[C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:5][CH2:4][NH2:1]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-(2-azidoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indole (0.400 g; 1.09 mmol) and triphenylphosphine (0.427 g; 1.63 mmol) in methanol (5 mL) was stirred at 70° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and the crude material was dissolved in a solution of tetrabutylamonium fluoride (3.26 mL, 1M) in THF, stirred at room temperature for 36 hours, and concentrated under reduced pressure. The crude material was used without any further purification.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
dissolutionthe crude material was dissolved in a solution of tetrabutylamonium fluoride (3.26 mL, 1M) in THF
stirringstirred at room temperature for 36 hours
concentrationconcentrated under reduced pressure
customThe crude material was used without any further purification

Sources & evidence

ORD record: ord-6a9b407d595d4ebb81db5c8e6da875a0
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266832B2

Reaction notes

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