Sodium hydride → HCID 67367235, compound

HRID 1753120Notes

Reaction equation

HRID 1753120 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[H-].[Na+].Br.Br[CH2:14][C:15]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)=[O:16].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[O:16]=[C:15]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:14][N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 136930Methyl pyrrole-2-carboxylateHCID 27762343-(2-Bromoacetyl)pyridine hydrobromide

Product 1

HCID 67367235HCID 67367235, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a chilled solution of methyl 2-pyrrole carboxylate (200 mg, 1.6 mmol) in dry DMF (5 mL) was added sodium hydride (60% dispersion in mineral oil, 160 mg, 4.0 mmol) portionwise under nitrogen. Extra DMF (2 mL) was added and the suspension was stirred for 30 minutes. 3-(Bromoacetyl)pyridine hydrobromide (600 mg, 2.1 mmol) was added portionwise and the mixture was allowed at room temperature and stirred overnight. Saturated aqueous solution of aqueous NH4Cl (10 mL) followed by EtOAc (30 mL) were added. The organic layer was washed with brine (10 mL), dried (MgSO4), filtered and concentrated in vacuo to give an orange liquid that was purified by flash chromatography (Biotage SP4, 40 g cartridge, gradient 0-80% EtOAc in hexanes) to yield methyl 1-[2-oxo-2-(pyridin-3-yl)ethyl]-1H-pyrrole-2-carboxylate as a colourless oil (75 mg, yield 19%). 1H-NMR (400 MHz, CDCl3): δ 3.72 (s, 3H), 5.72 (s, 2H), 6.26 (dd, 1H, J 4.0, 2.6 Hz), 6.85 (dd, 1H, J 2.6, 1.8 Hz), 7.04 (dd, 1H, J 4.0, 1.8 Hz), 7.46 (ddd, 1H, J 7.9, 4.8, 0.8 Hz), 8.25-8.28 (m, 1H), 8.83 (dd, 1H, J 4.8, 1.7 Hz), 9.21 (dd, 1H, J 0.8, 2.2 Hz).

Workup

  1. customwas allowed at room temperature
  2. stirringstirred overnight
  3. additionwere added
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give an orange liquid that
  9. customwas purified by flash chromatography (Biotage SP4, 40 g cartridge, gradient 0-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fdd6336062304c158ec7c489a288e383
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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