HCID 86718025, compound → HCID 86718026, compound

HRID 1500488Notes

Reaction equation

HRID 1500488 reaction equation
[NH2:1][C:2]1[C:10]2[O:9][CH:8]([CH:11]([OH:13])C)[CH2:7][C:6]=2[C:5]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:4]([CH3:20])[CH:3]=1>CC(O)=O.O=[Pt]=O>[NH2:1][C:2]1[C:10]2[O:9][CH:8]([CH2:11][OH:13])[CH2:7][C:6]=2[C:5]([CH:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[C:4]([CH3:20])[CH:3]=1

Participants

4

Reactant 1

HCID 86718025HCID 86718025, compound

Product 1

HCID 86718026HCID 86718026, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of (7-amino-5-methyl-4-(pyridin-4-yl)-2,3-dihydrobenzofuran-2-yl)methanol (7f) (0.10 g, 0.39 mmol), PtO2 (50 mg, 50%) and TEA (0.061 mL, 0.78 mmol) in HOAc (5 mL) was introduced H2 and stirred at ambient temperature for 24 h (88 psi). The mixture was filtered, concentrated, and 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 (7g) as a yellow oil. MS-ESI (m/z): 262 (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, it
  6. extractionwas extracted with EtOAc (150 mL)
  7. washwashed with water, brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9ab687e1a8c64be0b97f691e64654f72
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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