HCID 67383071, compound → HCID 67383486, compound

HRID 335960Notes

Reaction equation

HRID 335960 reaction equation
[CH3:1][Mg]Cl.[CH3:4][N:5]([CH3:28])[C:6]1[N:11]=[CH:10][C:9]2[O:12][C:13]3[C:18]([C:19](=[O:20])[C:8]=2[CH:7]=1)=[CH:17][C:16]([C:21]1[C:22]([F:27])=[N:23][CH:24]=[CH:25][CH:26]=1)=[CH:15][CH:14]=3>C1COCC1>[CH3:4][N:5]([CH3:28])[C:6]1[N:11]=[CH:10][C:9]2[O:12][C:13]3[C:18]([C:19]([CH3:1])([OH:20])[C:8]=2[CH:7]=1)=[CH:17][C:16]([C:21]1[C:22]([F:27])=[N:23][CH:24]=[CH:25][CH:26]=1)=[CH:15][CH:14]=3

Participants

4

Reactant 2

HCID 67383071HCID 67383071, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 67383486HCID 67383486, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methylmagnesium chloride, 22 wt % in THF (1.6 mL, 4.76 mmol), was added via syringe to a suspension of 3-(dimethylamino)-7-(2-fluoropyridin-3-yl)-5H-chromeno[2,3-c]pyridin-5-one (0.53 g, 1.57 mmol) in THF (16 mL) at 0° C. The resulting solution was stirred at 0° C. for 1 h. The reaction was quenched with saturated aqueous ammonium chloride at 0° C. and diluted with water and extracted with DCM. The combined organic extracts were washed with a 9:1 mixture of aqueous saturated ammonium chloride/ammonium hydroxide, water, saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel chromatography by eluting with 1:2 EtOAc in hexane, to provide 3-(dimethylamino)-7-(2-fluoropyridin-3-yl)-5-methyl-5H-chromeno[2,3-c]pyridin-5-ol as a yellow solid.

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride at 0° C.
  2. additiondiluted with water
  3. extractionextracted with DCM
  4. washThe combined organic extracts were washed with a 9:1 mixture of aqueous saturated ammonium chloride/ammonium hydroxide, water, saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customto give the crude material
  9. customThe crude material was purified by silica gel chromatography
  10. washby eluting with 1:2 EtOAc in hexane

Sources & evidence

ORD record
ord-a5ecee5adbc7407eb2b49e2cf305b82a
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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