Cesium carbonate → HCID 68749705, compound

HRID 588980Notes

Reaction equation

HRID 588980 reaction equation
CS(O[CH2:6][C:7]1[C:12]([CH2:13]OS(C)(=O)=O)=[CH:11][C:10]([Br:19])=[CH:9][N:8]=1)(=O)=O.[CH3:20][Si:21]([CH3:37])([CH3:36])[CH2:22][CH2:23][O:24][CH2:25][N:26]1[C:30]2=[N:31][CH:32]=[CH:33][CH:34]=[C:29]2[CH2:28][C:27]1=[O:35].C(=O)([O-])[O-].[Cs+].[Cs+]>C(O)C>[Br:19][C:10]1[CH:11]=[C:12]2[CH2:13][C:28]3([C:29]4[C:30](=[N:31][CH:32]=[CH:33][CH:34]=4)[N:26]([CH2:25][O:24][CH2:23][CH2:22][Si:21]([CH3:36])([CH3:20])[CH3:37])[C:27]3=[O:35])[CH2:6][C:7]2=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 574588861-{[2-(Trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-oneHCID 86665188(5-Bromopyridine-2,3-diyl)dimethanediyl dimethanesulfonate

Product 1

HCID 68749705HCID 68749705, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(5-Bromopyridine-2,3-diyl)dimethanediyl dimethanesulfonate (17.0 g, 45.4 mmol) was added to a mixture of 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (prepared according to the procedures described in WO2008/020902, 14.0 g, 53.0 mmol) and cesium carbonate (49.0 g, 150 mmol) in ethanol (500 mL) 23° C., and the resulting mixture was stirred for 20 h. The reaction mixture was concentrated then partitioned between ethyl acetate (500 mL) and water (500 mL). The organic layer was dried over magnesium sulfate and concentrated. The residue was purified via silica gel chromatography (heptane initially, grading to 100% EtOAc) to give the title compound. MS: m/z=448.1 (M+1).

Workup

  1. customprepared
  2. concentrationThe reaction mixture was concentrated
  3. customthen partitioned between ethyl acetate (500 mL) and water (500 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified via silica gel chromatography (heptane initially

Sources & evidence

ORD record
ord-0ff26d9f64b943e49753521a220196c0
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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