Sodium Hydroxide → HCID 21473615, compound

HRID 2294051Notes

Reaction equation

HRID 2294051 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:10]2)(=O)=O.[Cl:26][C:27]1[CH:28]=[C:29](OB(O)O)[CH:30]=[C:31]([Cl:33])[CH:32]=1.C(=O)([O-])O.[Na+].[OH-].[Na+]>C(COC)OC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:26][C:27]1[CH:28]=[C:29]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:10]3)[CH:30]=[C:31]([Cl:33])[CH:32]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 10091216Tert-butyl 6-(trifluoromethylsulfonyloxy)-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 222835213,5-Dichlorophenylboric acid

Product 1

HCID 21473615HCID 21473615, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 3.81 g of crude tert.-butyl 6-(trifluoromethanesulphonyloxy)-3,4-dihydro-1H-isoquinoline-2-carboxylate in 40 ml of dimethoxyethane was treated under argon with 2.01 g (0.0105 mol) of 3,5-dichlorophenylboric acid and 13.5 ml (0.027 mol) of an aqueous 2N sodium hydrogen carbonate solution. The mixture was saturated with argon, 0.578 g (0.00050 mol) of tetrakis-(triphenylphosphine)-palladium was added thereto and the mixture was boiled at reflux for 20 hours. The mixture was cooled, poured into 120 ml of an aqueous 2N sodium hydroxide solution and extracted with ethyl acetate. The residue was chromatographed over silica gel with cyclohexane/ethyl acetate 9:1 as the eluent. 3.42 g (90%) of tert.-butyl 6-(3,5-dichlorophenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate were obtained as a pale yellow dense oil.

Workup

  1. additionwas added
  2. temperatureat reflux for 20 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. customThe residue was chromatographed over silica gel with cyclohexane/ethyl acetate 9:1 as the eluent

Sources & evidence

ORD record
ord-b798a3a1c21c4178ade4796156e36506
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

Loading…