Cesium carbonate → HCID 46195427, compound

HRID 1965583Notes

Reaction equation

HRID 1965583 reaction equation
[CH3:1][N:2]1[C:19]2[CH:18]=[C:17]3[O:20][CH2:21][CH2:22][O:23][C:16]3=[CH:15][C:14]=2[C:4]2([C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]2=[O:13])[C:3]1=[O:24].C(=O)([O-])[O-].[Cs+].[Cs+].Br.Br[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1>CN(C)C=O.O.C(OCC)(=O)C>[CH3:1][N:2]1[C:19]2[CH:18]=[C:17]3[O:20][CH2:21][CH2:22][O:23][C:16]3=[CH:15][C:14]=2[C:4]2([C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[C:5]2=[O:13])[C:3]1=[O:24]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 46195426HCID 46195426, compound

Product 1

HCID 46195427HCID 46195427, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 6-methyl-2,3-dihydrospiro[1,4-dioxino[2,3-f]indole-8,3′-indole]-2′,7(1′H,6H)-dione (0.07 g, 0.21 mmol) in N,N-dimethylformamide (5 mL) was added cesium carbonate (0.20 g, 0.61 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, 2-(bromomethyl)pyridine hydrobromide (0.08 g, 0.31 mmol) was added and the mixture was stirred at ambient temperature for 18 h. The mixture was diluted with water and ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography and eluted with ethyl acetate/hexanes (3/2) to afford 6-methyl-1′-(pyridin-2-ylmethyl)-2,3-dihydrospiro[1,4-dioxino[2,3-f]indole-8,3′-indole]-2′,7(1H,6H)-dione (0.02 g, 26%): mp 87-89° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.64-8.63 (m, 1H), 7.71-7.62 (m, 2H), 7.26-7.17 (m, 2H), 6.96-6.47 (m, 3H), 6.47 (s, 1H), 6.46 (s, 1H), 5.33 (s, 2H), 4.24-4.06 (m, 4H), 3.22 (s, 3H); MS (ES+) m/z 414.0 (M+1).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 18 h
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluted with ethyl acetate/hexanes (3/2)

Sources & evidence

ORD record
ord-f89a3ce3034f429bb90c22eef1fcaba8
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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