Acetic Acid → HCID 89813688, compound

HRID 2172324Notes

Reaction equation

HRID 2172324 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=2[C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[CH:19]=[CH:20][N:21]=[CH:22]3)[CH:6]=1.C(O)(=O)C>CO.[Pt](=O)=O>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[C:11]([C:13]([F:15])([F:14])[F:16])[CH:10]=[CH:9][C:8]=2[C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[CH2:19][CH2:20][NH:21][CH2:22]3)[CH:6]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 89815042HCID 89815042, compound

Product 1

HCID 89813688HCID 89813688, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-(2-(4-methyl-1H-imidazol-1-yl)-4-(trifluoromethyl)phenyl)isoquinoline (1.435 g, 4.06 mmol) in 15 mL MeOH was treated with platinum(IV) oxide (0.092 g, 0.406 mmol) and acetic acid (0.697 ml, 12.18 mmol) and was placed under 45 psi (4559.6 kpa) H2 for 3 hours. The reaction mixture was filtered through a plug of diatomaceous earth eluting with EtOAc. The filtrate was concentrated then purified directly be reverse phase column chromatography [RediSep Gold C18 150 g, 5 to 100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] yielding 5-(2-(4-methyl-1H-imidazol-1-yl)-4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.808 g, 2.261 mmol).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of diatomaceous earth
  2. washeluting with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customthen purified directly be reverse phase column chromatography [RediSep Gold C18 150 g, 5 to 100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)]

Sources & evidence

ORD record
ord-d9efeadcbf114e989572ee1c7c0f40d2
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

Loading…