Pentane → HCID 178526263, compound

HRID 1881335Notes

Reaction equation

HRID 1881335 reaction equation
CCCCC.[H-].[Na+].[Br:8][C:9]1[N:14]=[C:13]2[CH2:15][C:16](=[O:18])[NH:17][C:12]2=[CH:11][CH:10]=1.Cl[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:22][N+:21]=1[O-:33]>CN(C=O)C>[Br:8][C:9]1[N:14]=[C:13]2[C:15]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)=[CH:22][N+:21]=3[O-:33])=[C:16]([OH:18])[NH:17][C:12]2=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 210185645-Bromo-1,3-dihydro-2H-pyrrolo[3,2-B]pyridin-2-oneHCID 85873132HCID 85873132, compound

Product 1

HCID 178526263HCID 178526263, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of previously pentane-washed sodium hydride on mineral oil (75 mg, 1.88 mmol) in DMF (2 mL) was added slowly 5-bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (300 mg, 1.41 mmol). The resulting green solution was further stirred for 10 minutes at RT. Then a solution of 215 mg (0.939 mmol) of 2-chloro-5-(morpholinomethyl)-pyridine 1-oxide prepared like in example 2.2 in DMF was added and the resulting mixture was heated to 130° C. and stirred for further 30 min. The reaction was cooled to RT and all volatiles were removed under reduced pressure. The residue was taken up in 2 M HCl (60 mL) and washed with ethyl acetate. The aqueous layer was carefully saturated with solid NaHCO3 and extracted with ethyl acetate. The combined organic phases were dried over MgSO4, filtered, and evaporated yielding the titled compound as a red oil.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated to 130° C.
  3. stirringstirred for further 30 min
  4. temperatureThe reaction was cooled to RT
  5. customall volatiles were removed under reduced pressure
  6. washwashed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. dry with materialThe combined organic phases were dried over MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-80cc59c7d8324bd59e30153683944908
Source dataset
uspto-grants-2012_11
Patent number
US08318793B2

Reaction notes

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