Potassium Phosphate, Tribasic → 3-Methanesulfonyl-2-methyl-4-morpholin-4-yl-6-((1R,2R)-2-phenyl-cyclopropyl)-quinoline

HRID 13660Notes

Reaction equation

HRID 13660 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:5]2[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.[C:23]1([C@@H:29]2[CH2:31][C@H:30]2B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:16][S:13]([C:6]1[C:7]([CH3:12])=[N:8][C:9]2[C:4]([C:5]=1[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[CH:3][C:2]([C@@H:30]1[CH2:31][C@H:29]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:11][CH:10]=2)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 11062695Trans-2-phenylcyclopropylboronic acidHCID 120018106-Bromo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline2×

Product 1

HCID 120018033-Methanesulfonyl-2-methyl-4-morpholin-4-yl-6-((1R,2R)-2-phenyl-cyclopropyl)-quinolineYield 61.3%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

6-Bromo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline (compound of example 6) (300 mg, 0.78 mmol), trans-2-phenylcyclopropylboronic acid (189 mg, 1.17 mmol), potassium phosphate (496 mg, 2.33 mmol) and tetrakis(triphenylphosphine)-palladium (27 mg, 0.023 mmol) were heated at reflux under argon for 8 h. The crude product was purified by chromatography on silica gel in dichloromethane/ethyl acetate 5:1 with a gradient from 100:0 to 80:20. One obtained 202 mg (60%) of white crystals. MS: m/z=423 (M+H).

Workup

  1. temperatureat reflux under argon for 8 h
  2. customThe crude product was purified by chromatography on silica gel in dichloromethane/ethyl acetate 5:1 with a gradient from 100:0 to 80:20

Sources & evidence

ORD record
ord-11d352aca3c44b14a156a9edbe2e1959
Source dataset
uspto-grants-2010_06
Patent number
US07728142B2

Reaction notes

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