Sodium Hydroxide → 6-(6,7-Dimethoxy-quinolin-4-ylmethyl)-naphthalen-2-ylamine

HRID 1925264Notes

Reaction equation

HRID 1925264 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][C:13]1[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][CH:14]=1)[CH:6]=[CH:5]2.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[Li+].C[Si]([N-:45][Si](C)(C)C)(C)C.[OH-].[Na+]>CCOCC.Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][C:19]=1[O:25][CH3:26])[N:16]=[CH:15][CH:14]=[C:13]2[CH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([NH2:45])[CH:11]=[CH:10]2

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2733832Lithium HexamethyldisilazideHCID 67520211HCID 67520211, compound

Product 1

HCID 675205706-(6,7-Dimethoxy-quinolin-4-ylmethyl)-naphthalen-2-ylamine

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a sealed tube, 4-(6-bromo-naphthalen-2-ylmethyl)-6,7-dimethoxy-quinoline (Step f, 100 mg, 0.11 mmol), Pd2(dba)3 (5 mg, 0.0055 mmol), P(t-Bu)3 (1.1 mg, 0.0055 mmol), toluene (1 mL) was combined under nitrogen, followed by addition of LiHMDS (1M in THF, 0.137 mL, 0.137 mmol). The reaction was stirred at RT overnight. The suspension was diluted with Et2O and HCl (1M, 1 mL) was added. The crude material was poured into 1N NaOH and extracted with Et2O 3×. The combined organic layer was washed with water and brine, dried on Na2SO4, filtered, concentrated and purified by prep-TLC with 100% EtOAc to give the desired compound. MS (ESI, pos. ion) m/z: 345.1 (M+1).

Workup

  1. additionwas added
  2. extractionextracted with Et2O 3×
  3. washThe combined organic layer was washed with water and brine
  4. customdried on Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by prep-TLC with 100% EtOAc

Sources & evidence

ORD record
ord-70d82cd6d9b04c35bc34b742a7b47a31
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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