Water → HCID 59321519, compound

HRID 2423529Notes

Reaction equation

HRID 2423529 reaction equation
N12CCCN=C1CCCCC2.[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:18](S(C1C=CC=CC=1)(=O)=O)[CH2:17][CH2:16]2.O>C1(C)C=CC=CC=1>[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:18][CH:17]=[CH:16]2

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59321554Ethyl 6-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate

Product 1

HCID 59321519HCID 59321519, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (762.3 μL, 5.10 mmol) was added to ethyl 6-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate (1.03 g, 2.43 mmol) in toluene (12 mL) under argon and the reaction was stirred for 18 hours. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:3 ethyl acetate:hexanes to give 400.6 mg (59%) of ethyl 6-bromo-1-isoquinolinecarboxylate as a solid. 1H NMR (400 MHz, d6-DMSO): δ 8.63 (d, J=6 Hz, 1H), 8.43 (d, J=2 Hz, 1H), 8.41 (d, J=10 Hz, 1H), 8.05 (d, J=6 Hz, 1H), 7.91 (dd, J=9, 2 Hz, 1H), 4.46 (q, J=7 Hz, 2H), 1.37 (t, J=7 Hz, 3H). ESI-LCMS m/z 280 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium bicarbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 1:3 ethyl acetate

Sources & evidence

ORD record
ord-fd4dab90cc7c45cbb5fb2780370ec196
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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