Cesium carbonate → HCID 136338042, compound

HRID 2174558Notes

Reaction equation

HRID 2174558 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:19])=[C:7]([C:13]3[O:17][N:16]=[C:15]([CH3:18])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1I.CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[N:36]=[C:37]([NH:40][C:41](=[O:43])[CH3:42])[S:38][CH:39]=3)=[CH:31][CH:30]=2)O1.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:19])=[C:7]([C:13]3[O:17][N:16]=[C:15]([CH3:18])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[C:29]1[CH:30]=[CH:31][C:32]([C:35]2[N:36]=[C:37]([NH:40][C:41](=[O:43])[CH3:42])[S:38][CH:39]=2)=[CH:33][CH:34]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 86706567HCID 86706567, compound2×HCID 136338043HCID 136338043, compound2×

Product 1

HCID 136338042HCID 136338042, compoundYield 85%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

To a solution of 7-chloro-4-hydroxy-6-iodo-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one (Intermediate 99) (125 mg, 0.311 mmol) in 1,4-dioxane (4 mL) and water (2 mL) were added N-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)thiazol-2-yl)acetamide (Intermediate 31) (118 mg, 0.342 mmol), cesium carbonate (152 mg, 0.466 mmol) and tetrakis(triphenylphosphine)palladium (3.59 mg, 3.11 μmol). The reaction mixture was heated at 80° C. for 16 h. After cooling the reaction mixture was filtered, evaporated to dryness. The resulting residue was acidified with HCl 1N. The precipitate was filtered and dried to give the title compound N-(4-(4-(7-chloro-4-hydroxy-3-(3-methylisoxazol-5-yl)-2-oxo-1,2-dihydro quinolin-6-yl)phenyl)thiazol-2-yl)acetamide (130 mg, 0.264 mmol, 85% yield) as a grey solid. LCMS: (M+H)+=493; Rt=2.37 min.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationwas filtered
  3. customevaporated to dryness
  4. filtrationThe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-bbbb84f1dde24bab8776b6842177a7f6
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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