Triphenylphosphine → 2-(5,6-Dichloro-1H-indol-3-yl)ethanamine

HRID 1777555Notes

Reaction equation

HRID 1777555 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:16])=[C:12]([Cl: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:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[Cl:16])[NH:8][CH:7]=[C:6]2[CH2:5][CH2:4][NH2:1]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 866993923-(2-Azidoethyl)-5,6-dichloro-2-(triethylsilyl)-1H-indole

Product 1

HCID 133016902-(5,6-Dichloro-1H-indol-3-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(2-azidoethyl)-5,6-dichloro-2-(triethylsilyl)-1H-indole (0.497 g; 1.35 mmol) and triphenylphosphine (0.529 g; 1.35 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 (4.04 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

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe crude material was dissolved in a solution of tetrabutylamonium fluoride (4.04 mL 1M) in THF
  3. stirringstirred at room temperature for 36 hours
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was used without any further purification

Sources & evidence

ORD record
ord-518fca3dfc114fe29036d55eddec0411
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

Loading…