Sodium hydride → HCID 90387563, compound

HRID 2170231Notes

Reaction equation

HRID 2170231 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].[CH:14]([Si:17]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])Cl)([CH3:16])[CH3:15]>O1CCCC1>[CH3:1][C:2]1[N:3]([Si:17]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:14]([CH3:16])[CH3:15])[CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylateHCID 139400Triisopropylsilyl chloride

Product 1

HCID 90387563HCID 90387563, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-methyl-1H-pyrrole-3-carboxylate (purchased from Beta Pharma Scientific, 9.91 g, 64.7 mmol) in tetrahydrofuran (200 mL) at 0° C. under N2 was treated portionwise with sodium hydride (dry, 95%) (2.06 g, 82 mmol). The resulting mixture was stirred for 20 minutes and treated with triisopropylchlorosilane (16.5 mL, 78 mmol). The mixture was stirred for 30 minutes, then the ice bath was removed. After warming to ambient temperature over 90 minutes, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous magnesium sulfate) filtered and concentrated. Purification by chromatography on a 330 g silica cartridge eluting with 0-20% ethyl acetate in hexane afforded the title compound.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. customthe ice bath was removed
  3. customthe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography on a 330 g silica cartridge
  9. washeluting with 0-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d46b04e15c9c4534933186fc00b7b605
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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