Water → (2-Methoxy-benzyl)-(5-phenyl-quinolin-2-yl)-amine

HRID 1170073Notes

Reaction equation

HRID 1170073 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[N:7]2.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 67334552(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine

Product 1

HCID 68433822(2-Methoxy-benzyl)-(5-phenyl-quinolin-2-yl)-amine

Reagents, catalysts & solvents 3

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

Procedure

(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (200 mg, 0.583 mmol) was dissolved in 8 mL 1,2-dimethoxyethane and 4 mL 1M sodium carbonate solution. The reaction mixture was evacuated and backfilled with argon for three times to remove oxygen. Phenylboronic acid (88 mg, 0.699 mmol), palladium(II)acetate (7 mg, 0.029 mmol) and triphenylphosphine (16 mg, 0.058 mmol) were added. The reaction mixture was refluxed overnight. The reaction mixture was poured into 100 mL water and extracted three times with ethyl acetate (100 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient). The title compound was obtained as a white solid (191 mg, 96%), MS: m/e=341.3 (M+H+).

Workup

  1. customThe reaction mixture was evacuated
  2. customto remove oxygen
  3. temperatureThe reaction mixture was refluxed overnight
  4. extractionextracted three times with ethyl acetate (100 mL each)
  5. dry with materialThe combined organic extracts were dried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient)

Sources & evidence

ORD record
ord-21d65a832b624175ad5713536a122c5a
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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