HCID 86718029, compound → HCID 86718017, compound

HRID 1500492Notes

Reaction equation

HRID 1500492 reaction equation
CO[CH2:3][CH:4]1[CH2:8][C:7]2[C:9](C3C=CN=CC=3)=[C:10]([CH3:14])[CH:11]=[C:12]([NH2:13])[C:6]=2[O:5]1>CC(O)=O.O=[Pt]=O>[CH3:3][C@H:4]1[CH2:8][C:7]2[CH:9]=[C:10]([CH3:14])[CH:11]=[C:12]([NH2:13])[C:6]=2[O:5]1

Participants

4

Reactant 1

HCID 86718029HCID 86718029, compound

Product 1

HCID 86718017HCID 86718017, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-(methoxymethyl)-5-methyl-4-(pyridin-4-yl)-2,3-dihydrobenzofuran-7-amine (8d) (0.57 g, 2.1 mmol), PtO2 (300 mg, 50%) and TEA (0.323 mL, 4.20 mmol) in HOAc (15 mL) was introduced H2 and stirred at ambient temperature for 24 h (88 psi). The mixture was filtered, concentrated, diluted with EtOAc (50 mL), a solution of ammonium hydroxide was added until pH=10. It was extracted with EtOAc (150 mL), washed with water, brine, dried and concentrated to give the title compound (5e) as a yellow oil. MS-ESI (m/z): 277 (M+1)+.

Workup

  1. additionwas introduced H2
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. additiondiluted with EtOAc (50 mL)
  5. additiona solution of ammonium hydroxide was added until pH=10
  6. extractionIt was extracted with EtOAc (150 mL)
  7. washwashed with water, brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-34b9b4bc552f41d78dd8383de7eb8af8
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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