Cesium carbonate → HCID 68291181, compound

HRID 2174561Notes

Reaction equation

HRID 2174561 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:18])=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1I.[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][C:26](B(O)O)=[CH:27][CH:28]=2)[CH:23]=[CH:22]1.C(=O)([O-])[O-].[Cs+].[Cs+]>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>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:18])=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[C:26]1[CH:25]=[C:24]2[C:29](=[CH:28][CH:27]=1)[N:21]([CH3:20])[CH:22]=[CH:23]2

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27598671-Methyl-1H-indole-5-boronic acidHCID 68291064HCID 68291064, compound2×

Product 1

HCID 68291181HCID 68291181, compoundYield 65.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of ethyl 7-chloro-4-hydroxy-6-iodo-2-oxo-1,2-dihydro-3-quinolinecarboxylate (Intermediate 100) (300 mg, 0.762 mmol) in 1,4-dioxane (7 mL) and water (3.5 mL) were added (1-methyl-1H-indol-5-yl)boronic acid (Combi-Blocks, 140 mg, 0.800 mmol), cesium carbonate (373 mg, 1.143 mmol) and tetrakis(triphenylphosphine)palladium (8.81 mg, 7.62 μmol). The reaction vessel was sealed and heated to 120° C. for 20 min in a microwave. After cooling, the mixture was filtered, evaporated to dryness and the resulting residue was acidified with 1N HCl. The precipitate was filtered and dried to give ethyl 7-chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydro-3-quinolinecarboxylate (198 mg, 0.499 mmol, 65.5% yield) as off-white solid. LCMS: (M+H)+=397; Rt=2.79 min. HRMS: calculated for C21H18ClN2O4 (M+H)+: 397.0955. found: 397.0927.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customevaporated to dryness
  5. filtrationThe precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-f1d9ed46f5864d72a27d772b41f3ae66
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

Loading…