Sodium Carbonate → HCID 86587705, compound

HRID 33282Notes

Reaction equation

HRID 33282 reaction equation
Br[C:2]1[NH:3][C:4]2[C:5]3[C:6]=1[CH2:7][NH:8][C:9](=[O:14])[C:10]=3[CH:11]=[CH:12][CH:13]=2.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+].[Li+].[Cl-]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:15]1([N:3]2[C:4]3[C:5]4[C:6]([CH2:7][NH:8][C:9](=[O:14])[C:10]=4[CH:11]=[CH:12][CH:13]=3)=[CH:2]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 98814392-Bromo-3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5-(1H)-one

Product 1

HCID 86587705HCID 86587705, compoundYield 93.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a suspension of 2 (0.1065 g, 0.424 mmol) in 20 mL toluene/10 mL EtOH was added phenylboronic acid (0.08 g, 0.636 mmol), Na2CO3 (0.113 g, 1.06 mmol) dissolved in a minimum amount of water, LiCl (0.054 g, 1.27 mmol), and tetrakis(triphenylphosphine)palladium(0) (24.5 mg, 21.0 μmol). The reaction mixture was refluxed for 16 h. The solvent was removed in vacuo, and the residue was taken up in EtOAc and washed with saturated aqueous NaHCO3, H2O, and brine. The organic layer was dried over Na2SO4 and concentrated to give a yellow solid, which was purified by flash column chromatography eluting with a gradient of 20% of EtOAc in hexanes to give 0.098 g of a mixture of 3 as a yellow solid. mp 215-218° C. (dec); 1H NMR (DMSO-d6) δ 5.04 (s, 2H), 7.17 (t, 1H, J=7.5 Hz), 7.34 (d, 1H, J=6.6 Hz), 7.35 (d, 1H, J=7.4 Hz), 7.50 (m, 4H), 7.66 (d, 1H, J=7.7 Hz), 7.84 (s, 1H), 11.64 (s, 1H); HRMS (M+H) 249.1023.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customThe solvent was removed in vacuo
  3. washwashed with saturated aqueous NaHCO3, H2O, and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give a yellow solid, which
  7. customwas purified by flash column chromatography
  8. washeluting with a gradient of 20% of EtOAc in hexanes

Sources & evidence

ORD record
ord-45c2e9abb764453ab52c7cafac6aa0b6
Source dataset
uspto-grants-2008_09
Patent number
US07429578B2

Reaction notes

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