Water → HCID 68194421, compound

HRID 1520173Notes

Reaction equation

HRID 1520173 reaction equation
Br[C:2]1[C:11]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([F:22])=[CH:19][CH:20]=3)[CH2:15][CH2:14][CH2:13]2)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]([O:25][CH3:26])=[O:24])[CH:8]=2)[N:3]=1.[CH3:27][C:28]1[NH:29][C:30]2[C:35]([CH:36]=1)=[CH:34][C:33](B1OC(C)(C)C(C)(C)O1)=[CH:32][CH:31]=2.C(=O)([O-])[O-].[Na+].[Na+].O>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>[F:22][C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[N:12]([C:11]1[C:2]([C:33]3[CH:34]=[C:35]4[C:30](=[CH:31][CH:32]=3)[NH:29][C:28]([CH3:27])=[CH:36]4)=[N:3][C:4]3[C:9]([N:10]=1)=[CH:8][C:7]([C:23]([O:25][CH3:26])=[O:24])=[CH:6][CH:5]=3)[CH2:13][CH2:14][CH2:15]2

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 184506482-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indoleHCID 86670036HCID 86670036, compound

Product 1

HCID 68194421HCID 68194421, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 2-bromo-3-(6-fluoro-1,2,3,4-tetrahydroquinolin-1-yl)quinoxaline-6-carboxylate (200 mg, 0.48 mmol) in ethylene glycol dimethyl ether (7 ml) was added 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (124 mg, 0.48 mmol), sodium carbonate (101.8 mg, 0.96 mmol) and Pd(PPh3)4 (28 mg, 0.02 mmol) and water (3 ml). The reaction was stirred for 40 min at 90° C. Then it was extracted with ethyl acetate (3×50 ml) and the organic layers were combined, dried over anhydrous magnesium sulfate and concentrated in vacuo to provide a residue, which was purified by a silica gel column chromatography with 2% ethyl acetate in petroleum ether to afford methyl 3-(6-fluoro-1,2,3,4-tetrahydroquinolin-1-yl)-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carboxylate as a light red solid (118 mg, 53%).

Workup

  1. extractionThen it was extracted with ethyl acetate (3×50 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto provide a residue, which
  5. customwas purified by a silica gel column chromatography with 2% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-3c208b7041394e74b6b5612705d3f574
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

Loading…