Dibutyltin oxide → HCID 178425707, compound

HRID 2175265Notes

Reaction equation

HRID 2175265 reaction equation
[CH3:1][C:2]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:20]#[N:21])[C:14]=2[CH2:13][CH2:12][CH2:11]1)=[O:9].C([Sn](CCCC)=O)CCC.[Si]([N:41]=[N+:42]=[N-:43])(C)(C)C>COCCOC>[NH:41]1[C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:14]=2[CH2:13][CH2:12][CH2:11][N:10]3[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:22]=[CH:23][CH:24]=[C:25]([CH3:26])[C:2]=2[CH3:1])=[N:21][N:43]=[N:42]1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 709826251-(4-(2,3-Dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinoline-5-carbonitrile

Product 1

HCID 178425707HCID 178425707, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinoline-5-carbonitrile (0.020 g, 0.057 mmol), dibutylstannanone (2.86 mg, 0.011 mmol) and TMS-N3 (0.030 mL, 0.230 mmol) in DME (0.3 mL) was stirred at 100° C. for 3 days, and then concentrated in vacuo. The resulting residue was purified by preparative HPLC (PHENOMENEX® Axia Luna column, 5μ, C18, 30×75 mm; 10 min gradient from 75% A:25% B to 0% A:100% B (A=90% H2O/10% MeCN+0.1% TFA); (B=90% MeCN/10% H2O+0.1% TFA); detection at 220 nm) to afford the title compound (18.7 mg, 82% yield) as an off-white solid. LCMS, [M+H]+=392.1.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was purified by preparative HPLC (PHENOMENEX® Axia Luna column
  3. custom10 min gradient

Sources & evidence

ORD record
ord-263f73189d6b4894ada1a5d69233280e
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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