Cesium carbonate → HCID 58118694, compound

HRID 1615814Notes

Reaction equation

HRID 1615814 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:4]=1[CH2:10]Br.[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+]>CO>[Br:9][C:6]1[CH:5]=[C:4]2[C:3](=[CH:8][CH:7]=1)[CH2:2][C:20]1([C:21]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[N:18]([CH2:17][O:16][CH2:15][CH2:14][Si:13]([CH3:28])([CH3:12])[CH3:29])[C:19]1=[O:27])[CH2:10]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 124964654-Bromo-1,2-bis(bromomethyl)benzeneHCID 574588861-{[2-(Trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one2×

Product 1

HCID 58118694HCID 58118694, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,2-bis(bromomethyl)-4-bromobenzene (40.9 g, 132 mmol) and 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (31.5 g, 119 mmol, described in Intermediate 4) in MeOH (2 L) was added cesium carbonate (129 g, 397 mmol), portionwise, over 5 min. After 18 h, the mixture was concentrated to a volume of about 500 mL, then partitioned between EtOAc (1.5 L) and H2O (1 L). The organic layer was washed with H2O (1 L), then brine (500 mL), then dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=445 (M+1).

Workup

  1. waitAfter 18 h
  2. concentrationthe mixture was concentrated to a volume of about 500 mL
  3. custompartitioned between EtOAc (1.5 L) and H2O (1 L)
  4. washThe organic layer was washed with H2O (1 L)
  5. dry with materialbrine (500 mL), then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-997112e069ea4e38a271ff05d159c2b6
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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