Trimethylphosphine → HCID 58565367, compound

HRID 2175329Notes

Reaction equation

HRID 2175329 reaction equation
[N:1]([CH:4]([C:6]1[N:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:5])=[N+]=[N-].CP(C)C>O1CCCC1>[F:21][C:17]1[CH:16]=[C:15]([N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:14]=[C:6]2[CH:4]([NH2:1])[CH3:5])[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 68983TrimethylphosphineHCID 58565371HCID 58565371, compound

Product 1

HCID 58565367HCID 58565367, compoundYield 133.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(1-azidoethyl)-1-(3-fluorophenyl)-1H-indole (0.14 g, 0.50 mmol) in tetrahydrofuran (3 mL) was added 1.00 M trimethylphosphine in tetrahydrofuran (0.75 mL, 0.75 mmol). The mixture was stirred at room temperature for 1 hour. The mixture was concentrated to give crude product (0.17 g), which was used directly in the next step. LCMS calculated for C16H13FN(M-NH2)+: m/z=238.1. Found: 238.1.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-3735d0eee7ad43c4aac3b20a7631e380
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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