Potassium Hydroxide → HCID 68953661, compound

HRID 1971276Notes

Reaction equation

HRID 1971276 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9].[OH-].[K+].[N+:12]([CH2:14][C:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16])#[C-:13]>CO>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C@@H:8]1[O:9][CH:13]=[N:12][C@H:14]1[C:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 27629973-Bromopyridine-4-carboxaldehydeHCID 6455476Pyrrolidine, 1-(isocyanoacetyl)-

Product 1

HCID 68953661HCID 68953661, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

BAL 01028A was prepared in accordance with method D using 3-bromo-4-pyridinecarboxaldehyde (1.010 g, 5.43 mmol), KOH (0.305 g, 5.43 mmol) in methanol (5 mL) and 2-isocyano-1-pyrrolidin-1-yl-ethanone BLE 04134 (0.75 g, 5.43 mmol). The mixture was stirred at 0° C. until precipitation and concentrated. The mixture was partitioned between EtOAc (50 ml) and H2O (25 ml). The aqueous layer was extracted twice with EtOAc (25 mL). The EtOAc fractions were combined, washed twice with brine (2×25 mL), dried over MgSO4 and filtered. After evaporation and trans-(5-(3-bromopyridin-4-yl)-4,5-dihydrooxazol-4-yl)(pyrrolidin-1-yl)methanone BAL 01028A was obtained (1.20 g, 68% yield) as a white solid.

Workup

  1. customBAL 01028A was prepared in accordance with method D
  2. concentrationconcentrated
  3. customThe mixture was partitioned between EtOAc (50 ml) and H2O (25 ml)
  4. extractionThe aqueous layer was extracted twice with EtOAc (25 mL)
  5. washwashed twice with brine (2×25 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customAfter evaporation

Sources & evidence

ORD record
ord-39e29abe4a9d42878a9f5a45e0128319
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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