Acetic Acid → HCID 59239771, compound

HRID 881680Notes

Reaction equation

HRID 881680 reaction equation
Br[CH2:2][C:3]1[C:8]([CH2:9]Br)=[CH:7][N:6]=[C:5]([C:11]#[N:12])[CH:4]=1.[CH3:13][Si:14]([CH3:30])([CH3:29])[CH2:15][CH2:16][O:17][CH2:18][N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH2:21][C:20]1=[O:28].C(=O)([O-])[O-].[Cs+].[Cs+].C(O)(=O)C>CN(C=O)C>[O:28]=[C:20]1[N:19]([CH2:18][O:17][CH2:16][CH2:15][Si:14]([CH3:30])([CH3:29])[CH3:13])[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[C:21]21[CH2:9][C:8]1[CH:7]=[N:6][C:5]([C:11]#[N:12])=[CH:4][C:3]=1[CH2:2]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10796Cesium carbonateHCID 57417127HCID 57417127, compoundHCID 574588861-{[2-(Trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one2×

Product 1

HCID 59239771HCID 59239771, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,5-bis(bromomethyl)pyridine-2-carbonitrile from Step B (729 mg, 2.52 mmol) and 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (665 mg, 2.52 mmol, described in Intermediate 1) in DMF (75 mL) was added cesium carbonate (2.46 g, 7.55 mmol), portionwise, over 5 min. After 2 h, acetic acid (0.15 mL) was added and the mixture was concentrated to a volume of about 25 mL, then partitioned between CHCl3 (100 mL), saturated aqueous NaHCO3 (30 mL) and brine (50 mL). The organic layer was removed and the aqueous layer was extracted further with CHCl3 (100 mL). The combined organic extracts were 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=393 (M+1).

Workup

  1. waitAfter 2 h
  2. concentrationthe mixture was concentrated to a volume of about 25 mL
  3. custompartitioned between CHCl3 (100 mL), saturated aqueous NaHCO3 (30 mL) and brine (50 mL)
  4. customThe organic layer was removed
  5. extractionthe aqueous layer was extracted further with CHCl3 (100 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-5e888d5d0c794d0eabe6c62204e75489
Source dataset
uspto-grants-2015_03
Patent number
US08993588B2

Reaction notes

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