Sodium Bicarbonate → HCID 67205185, compound

HRID 2041728Notes

Reaction equation

HRID 2041728 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])O1.[CH3:20][CH:21]([O:23][C:24](=[O:41])[NH:25][C@H:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33](Br)[CH:34]=2)[N:29]([C:37](=[O:39])[CH3:38])[C@@H:28]([CH3:40])[CH2:27]1)[CH3:22].C([O-])(O)=O.[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O1CCOCC1>[C:37]([N:29]1[C:30]2[C:35](=[CH:34][C:33]([C:9]3[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=3)[C:12]([O:14][CH3:15])=[O:13])=[CH:32][CH:31]=2)[C@H:26]([NH:25][C:24]([O:23][CH:21]([CH3:22])[CH3:20])=[O:41])[CH2:27][C@@H:28]1[CH3:40])(=[O:39])[CH3:38]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27346513-Methoxycarbonylphenylboronic acid pinacol esterHCID 529350201-Methylethyl((cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

Product 1

HCID 67205185HCID 67205185, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A flask was charged with methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.355 g, 1.354 mmol), 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 100) (0.5 g, 1.354 mmol), a saturated NaHCO3 aqueous solution (1.5 mL, 1.354 mmol) and PdCl2(dppf)-CH2Cl2 adduct (0.111 g, 0.135 mmol) then filled with 1,4-dioxane (7 mL) and the resulting mixture was degassed by bubbling nitrogen into it then stirred at 100° C. for 1 h under microwave irradiation before being cooled to room temperature, filtered through celite and concentrated in vacuo. The residue was partioned between EtOAC (30 mL) and water (30 mL) and the layers were separated. The organic phase was washed with brine (30 mL), dried under MgSO4 and concentrated in vacuo. Purification of the residue on Sp4 using a 50 G silica cartridge (gradient:20 to 80% AcOEt in Hexanes) gave methyl 3-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]benzoate (319 mg, 55%).

Workup

  1. customthe resulting mixture was degassed
  2. customby bubbling nitrogen into it
  3. temperaturebefore being cooled to room temperature
  4. filtrationfiltered through celite and
  5. concentrationconcentrated in vacuo
  6. customthe layers were separated
  7. washThe organic phase was washed with brine (30 mL)
  8. customdried under MgSO4
  9. concentrationconcentrated in vacuo
  10. customPurification of the residue on Sp4

Sources & evidence

ORD record
ord-b4e91cb432b4408bab58c6e22ecf975a
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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