Hydrochloric Acid → HCID 90121153, compound

HRID 521707Notes

Reaction equation

HRID 521707 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.C([Mg]Cl)(C)C.[CH2:14]([N:17]([CH2:25][C:26](N(OC)C)=[O:27])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=[CH2:16].Cl>O1CCCC1.C(OCC)(=O)C>[CH2:14]([N:17]([CH2:25][C:26]([C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1)=[O:27])[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH:15]=[CH2:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 27831712-Bromo-5-fluoropyridineHCID 86697892tert-Butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamateHCID 178418918HCID 178418918, compound

Product 1

HCID 90121153HCID 90121153, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-5-fluoro-pyridine (2.46 g, 13.98 mmol) in tetrahydrofuran (20 mL) is added drop wise to isopropylmagnesium chloride (15 mL, 30.00 mmol of a 2M solution in tetrahydrofuran) with stirring under nitrogen at room temperature. The resulting reaction mixture is stirred at room temperature for 2 hours. tert-Butyl N-allyl-N-[2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate (3.4 g, 13.16 mmol) in tetrahydrofuran (15 mL) is then added drop wise at room temperature and the resulting mixture is stirred overnight. Dilute aqueous hydrochloric acid is added followed by ethyl acetate. The layers are separated and the aqueous phase is re-extracted with ethyl acetate. The combined organic extracts are dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure. The resulting residue is purified by silica gel column chromatography using a 0-40% gradient of acetone in iso-hexane to give the title compound (1.27 g, 33%). ES/MS (m/e): 317 (M+23).

Workup

  1. customThe resulting reaction mixture
  2. stirringis stirred at room temperature for 2 hours
  3. stirringthe resulting mixture is stirred overnight
  4. customThe layers are separated
  5. extractionthe aqueous phase is re-extracted with ethyl acetate
  6. dry with materialThe combined organic extracts are dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e649a3cf9153487fb4d0c7bc7bc993ac
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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