Triphenylphosphine → 2-(6-chloro-5-methyl-1H-indol-3-yl)ethanamine

HRID 1777550Notes

Reaction equation

[N:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:16])=[C:12]([CH3:15])[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>[Cl:16][C:11]1[CH:10]=[C:9]2[C:14]([C:6]([CH2:5][CH2:4][NH2:1])=[CH:7][NH:8]2)=[CH:13][C:12]=1[CH3:15]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-(2-azidoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole (0.654 g; 1.87 mmol) and triphenylphosphine (0.737 g; 2.81 mmol) in methanol (10 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 (5.62 mL 1M) in THF, stirred at room temperature for 36 hours, and concentrated under reduced pressure. The crude material was used without further purification.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
dissolutionthe crude material was dissolved in a solution of tetrabutylamonium fluoride (5.62 mL 1M) in THF
stirringstirred at room temperature for 36 hours
concentrationconcentrated under reduced pressure
customThe crude material was used without further purification

Sources & evidence

ORD record: ord-cf48f7cc11874df5ad8a227ae4d5a502
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266832B2

Reaction notes

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