Cesium carbonate → 2-((1H-indol-3-yl)methyl)-9-(quinolin-3-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41575Notes

Reaction equation

HRID 41575 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([N:11]2[CH2:42][CH2:41][C:14]3([C:19](=[O:20])[N:18]([CH2:21][C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24](S(C5C=CC(C)=CC=5)(=O)=O)[CH:23]=4)[CH2:17][CH2:16][CH2:15]3)[CH2:13][CH2:12]2)[CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CO.C(OCC)(=O)C>[NH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([CH2:21][N:18]2[CH2:17][CH2:16][CH2:15][C:14]3([CH2:13][CH2:12][N:11]([C:3]4[CH:2]=[N:1][C:10]5[C:5]([CH:4]=4)=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH2:42][CH2:41]3)[C:19]2=[O:20])=[CH:23]1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 672511379-(quinolin-3-yl)-2-((1-tosyl-1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one

Product 1

HCID 532597892-((1H-indol-3-yl)methyl)-9-(quinolin-3-yl)-2,9-diazaspiro[5.5]undecan-1-oneYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 9-(quinolin-3-yl)-2-((1-tosyl-1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one (60 mg, 0.1 mmol) and Cs2CO3 (150 mg, 0.46 mmol) in methanol (2 mL) was heated under reflux for 18 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound (31 mg, 71%). [1H NMR (600 MHz, DMSO-d6) ♀ ppm 10.94 (br. s., 1H), 8.86 (d, 1H), 7.86-7.83 (m, 1H), 7.77-7.75 (m, 1H), 7.56-7.52 (m, 2H), 7.48-7.43 (m, 2H), 7.34 (d, 1H), 7.28 (d, 1H), 7.06 (t, 1H), 6.95 (t, 1H), 4.64 (s, 2H), 3.77-3.68 (m, 2H), 3.19-3.13 (m, 2H), 3.06 (t, 2H), 2.30-2.19 (m, 2H), 1.80-1.72 (m, 2H), 1.72-1.63 (m, 2H), 1.60-1.50 (m, 2H); LCMS RtA=1.05 min, [M+H]+=425.3].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3c3c8020636447bb8e77f6cd8fdc980
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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