HCID 19921681, compound → HCID 19921660, compound

HRID 1463341Notes

Reaction equation

HRID 1463341 reaction equation
CC([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:17]=2)[NH:12][C:11]=1[Si](C)(C)C)(C)C>CC#N>[OH:6][CH2:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:17]=2)[NH:12][CH:11]=1

Participants

3

Reactant 1

HCID 19921681HCID 19921681, compound

Product 1

HCID 19921660HCID 19921660, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 3-[3-[(1,1-dimethylethyl)dimethylsilyloxy]prop-1-yl]-2-trimethylsilyl-1H-indole-5-carboxylate (5.0 g, 11.5 mmol), and aqueous 48% HF (1.9 g, 46.0 mmol) in 140 mL of MeCN was stirred at 23° C. for 3.5 h. The solution was quenched with 10% Na2CO3, and the organic material was extracted into ethyl acetate. The organic solution was dried (brine, MgSO4), filtered, and concentrated in vacuo. Silica gel chromatography (50-100% EtOAc-hexanes gradient) of the concentrate yielded the title compound (2.79 g, 98%) as a white crystalline solid: mp 111°-112° C. Anal. Calcd for C14H17N1O3 : C, 68.00; H, 6.93; N, 5.66. Found: C, 67.94; H, 6.78; N, 5.65.

Workup

  1. customThe solution was quenched with 10% Na2CO3
  2. extractionthe organic material was extracted into ethyl acetate
  3. dry with materialThe organic solution was dried (brine, MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9123f1b667547c38da3e88307150cb4
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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