Hydrochloric Acid → HCID 86636443, compound

HRID 1483712Notes

Reaction equation

HRID 1483712 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[C:7]([F:32])=[C:8]([CH:20]=[CH:21][C:22]=1[B:23]1[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]1)[O:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([O:18][CH3:19])[N:11]=1.Cl.O>O1CCCC1>[F:32][C:7]1[C:6]([CH:2]=[O:1])=[C:22]([B:23]2[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]2)[CH:21]=[CH:20][C:8]=1[O:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([O:18][CH3:19])[N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 67440028HCID 67440028, compound

Product 1

HCID 86636443HCID 86636443, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-(3-(1,3-dioxolan-2-yl)-2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2-methoxynicotinonitrile (2.18 g, 4.93 mmol) in tetrahydrofuran (6 mL) was added 3 M HCl (3 mL). The solution was refluxed for four hours. The solution was cooled to room temperature and water was added. The solution was extracted with ethyl acetate. The organic layer was washed with water, then washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure to give 6-(2-fluoro-3-formyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2-methoxynicotinonitrile (1.45 g, 74% yield).

Workup

  1. temperatureThe solution was refluxed for four hours
  2. extractionThe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-613cdd67322f4e9dae1c3252a53d160f
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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