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

HRID 2115774
Notes
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Reaction equation

HRID 2115774 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 313Hydrochloric AcidSolvent
HCID 1140TolueneSolvent
HCID 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-f496066638944e839ef66c8417b2d1d5
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07435823B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes