1,2-Dimethoxyethane → HCID 70976485, compound

HRID 882232Notes

Reaction equation

HRID 882232 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=2)[C@H:7]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=2)[CH2:6][C@@H:5]1[CH3:25])(=[O:3])[CH3:2].[CH3:26][O:27][C:28]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)=[O:29].C(=O)([O-])[O-].[K+].[K+].COCCOC>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.O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:33]3[CH:34]=[CH:35][C:30]([C:28]([O:27][CH3:26])=[O:29])=[CH:31][CH:32]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=2)[CH2:6][C@@H:5]1[CH3:25])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 70976811HCID 70976811, compound

Product 1

HCID 70976485HCID 70976485, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a flask charged with (2S,4R)-1-acetyl-6-bromo-2-methyl-N-(5-nitro-2-pyridinyl)-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 19) (4.1 g, 10.12 mmol), {4-[(methyloxy)carbonyl]phenyl}boronic acid (2.185 g, 12.14 mmol), tetrakis(triphenylphosphine)palladium(0) (1.169 g, 1.012 mmol) and potassium carbonate (4.19 g, 30.4 mmol) was added DME (50 mL) and water (10.0 mL) and the resulting mixture was stirred at 100° C. under nitrogen for 1 h then cooled to room temperature and concentrated in vacuo. The residue was partitioned between EtOAc and water and the layers were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified by chromatography eluting with an EtOAc/hexanes gradient, which gave methyl 4-((2S,4R)-1-acetyl-2-methyl-4-((5-nitropyridin-2-yl)amino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (4.3 g, 9.34 mmol, 92% yield) as an orange foam, LCMS (HpH, 2 min), Rt=1.13 min, MH+=461.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between EtOAc and water
  4. customthe layers were separated
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography
  8. washeluting with an EtOAc/hexanes gradient, which

Sources & evidence

ORD record
ord-238b447a07b44d2aadd3e9eed5d53ab8
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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