Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86658485, compound

HRID 335898Notes

Reaction equation

HRID 335898 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](=[CH:32][C:33]=1[F:34])[O:30][C:24]1[CH:25]=[N:26][C:27]([Cl:29])=[CH:28][C:23]=1[C:22]2([CH3:36])O.C(=O)(O)[O-].[Na+]>ClCCCl>[Br:18][C:19]1[CH:20]=[C:21]2[C:31](=[CH:32][C:33]=1[F:34])[O:30][C:24]1[CH:25]=[N:26][C:27]([Cl:29])=[CH:28][C:23]=1[C:22]2=[CH2:36]

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 86658486HCID 86658486, compound

Product 1

HCID 86658485HCID 86658485, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Pyridinium p-toluenesulfonate (0.023 g, 0.090 mmol) was added to a solution of 7-bromo-3-chloro-8-fluoro-5-methyl-5H-chromeno[2,3-c]pyridin-5-ol (0.619 g, 1.796 mmol) in DCE (7.19 mL) at 65° C. After 1.5 hours, the reaction was judged complete by LC/MS analysis and the solution was allowed to cool to rt and was poured into saturated sodium bicarbonate (50 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×25 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 afford 7-bromo-3-chloro-8-fluoro-5-methylene-5H-chromeno[2,3-c]pyridine which was used directly for the next reaction without further purification. MS m/z=327.9 [M+H].

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×25 mL)
  3. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e639546b35034b3dae542735abc40bad
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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