Ethyl Acetate → HCID 86658479, compound

HRID 335881Notes

Reaction equation

HRID 335881 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Br:18][C:19]1[CH:20]=[C:21]2[C:31](=[C:32]([F:34])[CH:33]=1)[O:30][C:24]1[CH:25]=[N:26][C:27]([Cl:29])=[CH:28][C:23]=1[C:22]2([CH3:36])O.CCOC(C)=O.C(=O)(O)[O-].[Na+]>ClCCCl>[Br:18][C:19]1[CH:20]=[C:21]2[C:31](=[C:32]([F:34])[CH:33]=1)[O:30][C:24]1[CH:25]=[N:26][C:27]([Cl:29])=[CH:28][C:23]=1[C:22]2=[CH2:36]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 86658478HCID 86658478, compound

Product 1

HCID 86658479HCID 86658479, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Pyridinium p-toluene-sulfonate (2.53 g, 10.06 mmol) was added to a solution of 7-bromo-3-chloro-9-fluoro-5-methyl-5H-chromeno[2,3-c]pyridin-5-ol (3.15 g, 9.14 mmol) in DCE (91 mL) at 55° C. The reaction was stirred 2.5 hours at which time TLC analysis (10:1 Hex/EtOAc) showed the reaction to be complete. The reaction was poured into saturated aqueous sodium bicarbonate (150 mL) and the layers were separated. The aqueous layer was extracted with CH2Cl2 (4×150 mL). The combined organic extracts were washed with saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude product 7-bromo-3-chloro-9-fluoro-5-methylene-5H-chromeno[2,3-c]pyridine which was concentrated and used without further purification. MS m/z=327.9 [M+H].

Workup

  1. customthe reaction
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with CH2Cl2 (4×150 mL)
  4. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1810012fdf45402dbb69c2bb9f0d5208
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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