Potassium Carbonate → HCID 86669228, compound

HRID 2041710Notes

Reaction equation

HRID 2041710 reaction equation
[CH3:1][CH:2]([O:4][C:5](=[O:22])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[N:10]([C:18](=[O:20])[CH3:19])[C@@H:9]([CH3:21])[CH2:8]1)[CH3:3].[CH:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)=[O:24].C([O-])([O-])=O.[K+].[K+]>C(O)C.C1(C)C=CC=CC=1.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>[CH3:1][CH:2]([O:4][C:5](=[O:22])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:28]3[CH:29]=[CH:30][C:25]([CH:23]=[O:24])=[CH:26][CH:27]=3)[CH:15]=2)[N:10]([C:18](=[O:20])[CH3:19])[C@@H:9]([CH3:21])[CH2:8]1)[CH3:3]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 529350201-Methylethyl((cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

Product 1

HCID 86669228HCID 86669228, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see intermediate 100) (1 g, 2.71 mmol) and 4-formylbenzeneboronic acid (0.487 g, 3.25 mmol) in ethanol (4.7 mL) and toluene (4.70 mL) was treated with K2CO3 (0.449 g, 3.25 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.156 g, 0.135 mmol). The resulting mixture was stirred under nitrogen at 90° C. for 16 h then was cooled to room temperature and concentrated in vacuovacuo. The residue was partitioned between water (8.5 mL) and EtOAc (3 mL) and the resulting biphasic mixture was stirred at room temperature for 30 min then the insoluble residue was filtered off and dried under house vacuo at 40° C. for 1 hr to give 1-methylethyl[(2S,4R)-1-acetyl-6-(4-formylphenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (1.0759 g, 2.59 mmol, 96% yield) as a light yellow solid.

Workup

  1. temperaturethen was cooled to room temperature
  2. concentrationconcentrated in vacuovacuo
  3. customThe residue was partitioned between water (8.5 mL) and EtOAc (3 mL)
  4. stirringthe resulting biphasic mixture was stirred at room temperature for 30 min
  5. filtrationthe insoluble residue was filtered off
  6. customdried under house vacuo at 40° C. for 1 hr

Sources & evidence

ORD record
ord-baae7109e46a4652a847437c030c062f
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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