Sodium Hydroxide → HCID 89650645, compound

HRID 1773946Notes

Reaction equation

HRID 1773946 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[C:14]([Cl:22])[CH:15]=[CH:16][C:17]=2Br)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][S:24]([O-:26])=[O:25].[Na+].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>CS(C)=O.[Cu]I>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[C:14]([Cl:22])[CH:15]=[CH:16][C:17]=2[S:24]([CH3:23])(=[O:26])=[O:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 89649186HCID 89649186, compound

Product 1

HCID 89650645HCID 89650645, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture under Ar of 5-bromo-8-chloro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (190 mg, 0.5 mmol, 1.0 eq.), sodium methanesulfinate (72 mg, 0.6 mmol, 1.2 eq.), L-proline (12 mg, 0.1 mmol, 0.2 eq.), 1M aq. NaOH soln. (0.1 mL, 0.1 mmol, 0.2 eq.), and copper (I) iodide (10 mg, 0.05 mmol, 0.1 eq.) in DMSO (5 mL) was stirred at 150° C. under microwave irradiations for 1 hour. The mixture was allowed to cool to r.t. and partitioned between AcOEt (125 mL), and H2O (125 mL). The layers were separated and the aq. phase was extracted with AcOEt (2×125 mL). The comb. org. phases were dried over MgSO4 and concentrated in vacuo. The residue was purified by prep. HPLC (column: Waters Xbridge, 30×75 mm, 10 um, UV/MS, acidic conditions) and evaporated to give the title compound as a colorless oil.

Workup

  1. custompartitioned between AcOEt (125 mL), and H2O (125 mL)
  2. customThe layers were separated
  3. extractionthe aq. phase was extracted with AcOEt (2×125 mL)
  4. dry with materialphases were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by prep
  7. customHPLC (column: Waters Xbridge, 30×75 mm, 10 um, UV/MS, acidic conditions) and evaporated

Sources & evidence

ORD record
ord-407f4e8c141a4247a09fe170bad3e1f6
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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