Potassium Carbonate → HCID 118094098, compound

HRID 515534Notes

Reaction equation

HRID 515534 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8]([S:12]([NH:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)(=[O:14])=[O:13])=[CH:7][C:6]([C:21]3[C:22]([CH3:27])=[N:23][O:24][C:25]=3[CH3:26])=[CH:5][C:4]=2[N:3]=1.[CH:28]1(B(O)O)[CH2:30][CH2:29]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH:16]1([NH:15][S:12]([C:8]2[C:9]3[CH:10]=[CH:11][C:2]([CH:28]4[CH2:30][CH2:29]4)=[N:3][C:4]=3[CH:5]=[C:6]([C:21]3[C:22]([CH3:27])=[N:23][O:24][C:25]=3[CH3:26])[CH:7]=2)(=[O:14])=[O:13])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 118094028HCID 118094028, compound

Product 1

HCID 118094098HCID 118094098, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-chloro-N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)quinoline-5-sulfonamide (23 mg, 0.057 mmol), cyclopropaneboronic acid (50 mg, 10 equiv) dppf PdCl2 (8 mg, 20 mol %), potassium carbonate (60 mg) and dioxane (1 mL) was purged with nitrogen and heated at 110° C. for 1 hour. The reaction mixture was concentrated and purified by preparative HPLC to give the desired product, N-cyclopentyl-2-cyclopropyl-7-(3,5-dimethylisoxazol-4-yl)quinoline-5-sulfonamide.

Workup

  1. customwas purged with nitrogen
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-8502518694444d449037fdefc753ccb4
Source dataset
uspto-grants-2015_08
Patent number
US09108953B2

Reaction notes

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