Hydrochloric Acid → Hydrochloric Acid

HRID 1925246Notes

Reaction equation

HRID 1925246 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21](Br)[CH:22]=2)[C:17]=1[F:27].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[Li+].C[Si]([N-:46][Si](C)(C)C)(C)C.[ClH:51]>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>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([F:27])=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH2:46])[CH:20]=[CH:19]2.[ClH:51]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2733832Lithium HexamethyldisilazideHCID 675205642-(6,7-Dimethoxy-4-quinolyloxy)-6-bromo-1-fluoronaphthalene

Product 2

HCID 313Hydrochloric AcidHCID 675203606-(6,7-Dimethoxy-4-quinolyloxy)-5-fluoro-2-naphthylamine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-(6,7-dimethoxy-4-quinolyloxy)-6-bromo-1-fluoronaphthalene (Step b, 1.7 g, 4.0 mmol), Pd2(dba)3 (183 mg, 0.2 mmol, Aldrich) and P(t-Bu)3 (40 mg, 0.2 mmol, Aldrich) in a two-necked round-bottom flask was degassed under vacuum and refilled with N2. Under N2, dry toluene and LiHMDS (5 mL, 1M in THF, 5.0 mmol, Aldrich) was added to the mixture via syringe. The reaction was stirred at RT under N2 for 16 h. To the reaction was added 1N aqueous HCl (10 mL) and a yellow precipitate was collected by filtration. The solid was washed with 10 mL of water and dried in vacuo at 50° C. for 24 h to give title compound as HCl salt in the form of yellow solid. MS (ESI, pos. ion) m/z: 365 (M+1). Mass Calc'd for C21H17FN2O3: 364.12.

Workup

  1. customwas degassed under vacuum
  2. additionrefilled with N2
  3. filtrationa yellow precipitate was collected by filtration
  4. washThe solid was washed with 10 mL of water
  5. customdried in vacuo at 50° C. for 24 h

Sources & evidence

ORD record
ord-ecc294d356224557b99b4a48bfb28463
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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