Trimethylphosphine → HCID 58565355, compound

HRID 2175319Notes

Reaction equation

HRID 2175319 reaction equation
[N:1]([CH:4]([C:6]1[N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([Cl:15])[CH:9]=2)[CH3:5])=[N+]=[N-].CP(C)C>O1CCCC1>[Cl:15][C:10]1[CH:9]=[C:8]2[C:13]([CH:14]=[C:6]([CH:4]([NH2:1])[CH3:5])[N:7]2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 68983TrimethylphosphineHCID 58565360HCID 58565360, compound

Product 1

HCID 58565355HCID 58565355, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(1-azidoethyl)-6-chloro-1-(3-fluorophenyl)-1H-indole (55 mg, 0.17 mmol) in tetrahydrofuran (2 mL) was added 1.00 M of trimethylphosphine in tetrahydrofuran (0.26 mL, 0.26 mmol) and the resultant mixture was stirred at room temperature for 1 hour. The mixture was concentrated to give the desired amine (50 mg). The crude product was used directly in the next step. LCMS calculated for C16H12ClFN(M-NH2)+: m/z=272.1. Found: 272.0.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-b6fad8d1e7e443fc947c9f283c65df35
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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