Triphenylphosphine → (6-Chloro-4-pyridin-3-yl-quinolin-2-yl)-(2-methoxy-benzyl)-amine

HRID 1949022Notes

Reaction equation

HRID 1949022 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[CH:3]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])[CH:3]=[C:2]2[C:25]1[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 27343783-Pyridinylboronic acidHCID 68574963(4-Bromo-6-chloro-quinolin-2-yl)-(2-methoxy-benzyl)-amine

Product 1

HCID 68574847(6-Chloro-4-pyridin-3-yl-quinolin-2-yl)-(2-methoxy-benzyl)-amine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

(4-Bromo-6-chloro-quinolin-2-yl)-(2-methoxy-benzyl)-amine (530 mg, 1.4 mmol) and pyridine-3-boronic acid (224 mg, 1.8 mmol) were dissolved in 16 mL dimethoxyethane and 8 mL 2N sodium carbonate solution. The reaction mixture was evacuated and backfilled with argon for three times. Triphenylphosphine (37 mg, 0.141 mmol) and palladium acetate (16 mg, 0.071 mmol) were added and the mixture was refluxed overnight. The mixture was extracted three times with ethyl acetate (200 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->30:70 gradient). (6-Chloro-4-pyridin-3-yl-quinolin-2-yl)-(2-methoxy-benzyl)-amine was obtained as a white foam (500 mg, 94%), MS: m/e=376.4 (M+H+).

Workup

  1. customThe reaction mixture was evacuated
  2. temperaturethe mixture was refluxed overnight
  3. extractionThe mixture was extracted three times with ethyl acetate (200 mL each)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->30:70 gradient)

Sources & evidence

ORD record
ord-563f7d21d34f42e09dd7846450427068
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Reaction notes

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