Hydrochloric Acid → HCID 178487711, compound

HRID 880775Notes

Reaction equation

HRID 880775 reaction equation
[Cl:1][C:2]1[C:3]([O:31][CH3:32])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[N:13]1)[CH:8]=[C:7]2[O:21]CC1C=CC(OC)=CC=1.[Na+].[I-].O.Cl>C(#N)C>[Cl:1][C:2]1[C:3]([O:31][CH3:32])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]1[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[N:13]1)[CH:8]=[C:7]2[OH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5238Sodium IodideHCID 566051548-chloro-7-methoxy-4-(4-methoxy-benzyloxy)-2-(3-trifluoromethyl-1H-pyrazol-1-yl)-quinoline

Product 1

HCID 178487711HCID 178487711, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 234a (800 mg, 1 eq.), CeCl3.7H2O (965 mg, 1.5 eq.), and NaI (258 mg, 1 eq.) in ACN (10 mL) were stirred at 85° C. for 1 hr under microwave irradiation. Water was added and the mixture was acidified with 1N HCl to pH 5. The reaction mixture was extracted with diethyl ether. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (MeOH/DCM) to give compound 236a as a beige solid in 96% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 4.02 (s, 3H), 7.07 (s, 1H), 7.43 (s, 1H), 7.51 (d, J=9.11 Hz, 1H), 8.11 (d, J=9.11 Hz, 1H), 8.88 (s, 1H); MS (ESI, EI+) m/z=343.9 (MH+).

Workup

  1. extractionThe reaction mixture was extracted with diethyl ether
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by chromatography on silica gel (MeOH/DCM)

Sources & evidence

ORD record
ord-7172dd1fee2d4b23ac7096e7b9286f09
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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