Cesium carbonate → HCID 53318822, compound

HRID 1921234Notes

Reaction equation

HRID 1921234 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][C:13]1[CH:14]=[C:15]([C:24]([O:26]CC)=[O:25])[C:16](=[O:23])[N:17]3[C:22]=1[CH:21]=[CH:20][CH:19]=[CH:18]3)[CH2:6][CH2:5]2.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[O:23]=[C:16]1[N:17]2[C:22]([CH:21]=[CH:20][CH:19]=[CH:18]2)=[C:13]([CH2:12][N:7]2[CH2:6][CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:3]=3)[CH2:8]2)[CH:14]=[C:15]1[C:24]([OH:26])=[O:25]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 58157157HCID 58157157, compound

Product 1

HCID 53318822HCID 53318822, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 1-[(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)methyl]-4-oxo-4H-quinolizine-3-carboxylate (0.045 g, 0.10 mmol), phenylboronic acid (0.019 g, 0.15 mmol), and 1 N cesium carbonate (0.20 mL, 0.20 mmol) in 1 mL THF under nitrogen was added bis (tri-tert-butyl-phosphine)palladium(0) (10 mol %). The reaction mixture was stirred at 100° C. for 3 hours, then cooled to rt and concentrated in vacuo. To a solution of the resultant brown residue in 1 mL DMSO was added saturated aqueous lithium hydroxide (0.3 mL). After 2 hours, the reaction was filtered and subjected to purification via reverse phase HPLC to provide the title compound which gave a mass ion (ES+) of 411.0. 1H NMR (400 MHz, DMSO) δ 10.2 (br s, 1H), 9.46 (d, J=6.2 Hz, 1H), 8.74 (s, 1H), 8.60-8.56 (m, 1H), 8.32-8.08 (m, 2H), 7.78-7.75 (m, 1H), 7.67-7.65 (m, 2H), 7.57-7.55 (m, 1H), 7.48-7.44 (m, 2H), 7.38 (d, J=7.4 Hz, 1H), 7.32-7.12 (m, 1H), 4.94 (s, 2H), 4.64-4.50 (m, 2H), 3.82-3.38 (m, 2H), 3.18-3.07 (m, 2H).

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated in vacuo
  3. additionTo a solution of the resultant brown residue in 1 mL DMSO was added saturated aqueous lithium hydroxide (0.3 mL)
  4. waitAfter 2 hours
  5. filtrationthe reaction was filtered
  6. customsubjected to purification via reverse phase HPLC

Sources & evidence

ORD record
ord-6a8e1286eb7c4a79b1b8ca32b57042ab
Source dataset
uspto-grants-2012_05
Patent number
US08173672B2

Reaction notes

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