Sodium Carbonate → Ethyl 4-(3-methyl-5-nitro-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylate

HRID 1948113Notes

Reaction equation

HRID 1948113 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([CH3:12])[C:7]2=[O:13].CC1(C)C(C)(C)OB([C:25]2[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH:26]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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>[CH3:12][C:8]1[C:7](=[O:13])[C:6]2[C:11](=[C:2]([C:25]3[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH:26]=3)[CH:3]=[CH:4][C:5]=2[N+:14]([O-:16])=[O:15])[NH:10][CH:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 592787964-(4,4,5,5-Tetramethyl-(1,3,2)dioxaborolan-2-yl)cyclohex-3-ene-1-carboxylic acid ethyl esterHCID 672543158-bromo-3-methyl-5-nitroquinolin-4(1H)-one2×

Product 1

HCID 67254537Ethyl 4-(3-methyl-5-nitro-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylateYield 67%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 8-bromo-3-methyl-5-nitroquinolin-4(1H)-one (Compound 304E, 700 mg, 2.47 mmol), ethyl 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)cyclohex-3-enecarboxylate (1.8 g, 6.43 mmol, commercially available or can be prepared according to WO2008/099221), Pd(PPh3)4 (20 mg), and Na2CO3 (1 g, 9.43 mmol) in 1,4-dioxane/H2O (150 mL, 4:1) was evacuated and purged with N2. The reaction mixture was stirred at 100° C. for 18 h under N2. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The material was purified by flash column chromatography to afford the desired compound (600 mg, yield: 67%). 1H NMR (DMSO-d6, 400 MHz): δ=1.22 (t, J=7.2 Hz, 3H), 1.85 (m, 1H), 1.96 (s, 3H), 2.08 (m, 1H), 2.26 (m, 1H), 2.38-2.49 (m, 3H), 2.78 (m, 1H), 4.12 (q, J=7.2 Hz, 2H), 5.84 (s, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.83 (d, J=6.0 Hz, 1H), 10.94 (d, J=6.0 Hz, 1H).

Workup

  1. customcommercially available or can be prepared
  2. customwas evacuated
  3. custompurged with N2
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe material was purified by flash column chromatography

Sources & evidence

ORD record
ord-e74e190ebf334ffc950ee25c3139e633
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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