HCID 86658477, compound → HCID 86658478, compound

HRID 335880Notes

Reaction equation

HRID 335880 reaction equation
[CH3:1][Mg]Cl.[Br:4][C:5]1[CH:6]=[C:7]2[C:17](=[C:18]([F:20])[CH:19]=1)[O:16][C:10]1[CH:11]=[N:12][C:13]([Cl:15])=[CH:14][C:9]=1[C:8]2=[O:21]>C1COCC1>[Br:4][C:5]1[CH:6]=[C:7]2[C:17](=[C:18]([F:20])[CH:19]=1)[O:16][C:10]1[CH:11]=[N:12][C:13]([Cl:15])=[CH:14][C:9]=1[C:8]2([CH3:1])[OH:21]

Participants

4

Reactant 2

HCID 86658477HCID 86658477, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 86658478HCID 86658478, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl magnesium chloride, 22 wt % in tetrahydrofuran (6.14 mL, 18.26 mmol) was added to a solution of 7-bromo-3-chloro-9-fluoro-5H-chromeno[2,3-c]pyridin-5-one (3.0 g, 9.13 mmol) in THF (40 mL) at 0° C. After 2 hours, the reaction was quenched with saturated aqueous ammonium chloride (250 mL) and diluted with water (100 mL) and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with saturated aqueous ammonium chloride, water, 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-methyl-5H-chromeno[2,3-c]pyridin-5-ol which was used directly in the next reaction. MS m/z=346.0 [M+H].

Workup

  1. customthe reaction was quenched with saturated aqueous ammonium chloride (250 mL)
  2. additiondiluted with water (100 mL)
  3. extractionextracted with EtOAc (3×200 mL)
  4. washThe combined organic extracts were washed with saturated aqueous ammonium chloride, water, 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-a45f7c3726334ec987bec556d87b0c20
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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