Water → HCID 58118667, compound

HRID 1615847Notes

Reaction equation

HRID 1615847 reaction equation
Br[CH2:2][C:3]1[C:8]([CH2:9]Br)=[CH:7][N:6]=[C:5]([Cl:11])[CH:4]=1.[CH3:12][Si:13]([CH3:29])([CH3:28])[CH2:14][CH2:15][O:16][CH2:17][N:18]1[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH2:20][C:19]1=[O:27].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Cl:11][C:5]1[N:6]=[CH:7][C:8]2[CH2:9][C:20]3([CH2:2][C:3]=2[CH:4]=1)[C:21]1[C:22](=[N:23][CH:24]=[CH:25][CH:26]=1)[N:18]([CH2:17][O:16][CH2:15][CH2:14][Si:13]([CH3:28])([CH3:12])[CH3:29])[C:19]3=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 574588861-{[2-(Trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one2×HCID 86650287HCID 86650287, compound

Product 1

HCID 58118667HCID 58118667, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,5-bis(bromomethyl)-2-chloropyridine from Step D (254 mg, 0.85 mmol) and 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (226 mg, 0.86 mmol, described in Intermediate 4) in DMF (8 mL) was added cesium carbonate (455 mg, 1.40 mmol). After 21 h, the reaction mixture was poured into H2O (60 mL) and extracted with EtOAc (2×60 mL). The organic layer was washed with brine (40 mL), then dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexanes:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=402 (M+1).

Workup

  1. extractionextracted with EtOAc (2×60 mL)
  2. washThe organic layer was washed with brine (40 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexanes

Sources & evidence

ORD record
ord-8346ac7cebe24e30b01185140c3a2477
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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