Lithium Chloride → HCID 68707167, compound

HRID 222123Notes

Reaction equation

HRID 222123 reaction equation
Br.[CH2:2]([O:4][C:5]([C:7]1[C:19]2[CH2:18][CH2:17][C:16]3[CH:15]=[N:14][CH:13]=[CH:12][C:11]=3[C:10]=2[NH:9][C:8]=1Br)=[O:6])[CH3:3].[Li+].[Cl-]>CCO.C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:2]([O:4][C:5]([C:7]1[C:19]2[CH2:18][CH2:17][C:16]3[CH:15]=[N:14][CH:13]=[CH:12][C:11]=3[C:10]=2[NH:9][CH:8]=1)=[O:6])[CH3:3]

Participants

6

Reactant 2

HCID 433294Lithium ChlorideHCID 68705832HCID 68705832, compound

Product 1

HCID 68707167HCID 68707167, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-bromo-4,5-dihydro-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylic acid ethyl ester F1 (0.5 mmol), LiCl (1.49 mmol), Na2CO3.10H2O (1.74 mmol) and (Ph3P)2PdCl2 (0.005 mmol) in EtOH (4 mL) and toluene (4 mL) was heated with microwave irradiation to 150° C. for 20 min. The solvents were removed, DCM was added and the mixture washed with water. The organic layer was dried (Na2SO4), filtered and the solvent evaporated. The crude obtained was purified by chromatography on silica gel (DCM/MeOH 95:5). The title compound was obtained in 50% yield. ESI (+) MS: m/z 243 (MH+). 1H NMR: 1.29 (t, J=7.07, 3H), 2.83-3.00 (m, 4H), 4.20 (q, J=7.07, 2H), 7.42 (d, J=5.00, 1H), 7.59 (d, J=3.17, 1H), 8.29-8.42 (m, 2H), 12.22 (bs, 1H).

Workup

  1. customThe solvents were removed
  2. additionDCM was added
  3. washthe mixture washed with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe crude obtained
  8. customwas purified by chromatography on silica gel (DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-2501317d57e748e0904c2ed35002165c
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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