Tris(1,1-dimethylethyl)phosphine → HCID 59427360, compound

HRID 2359700Notes

Reaction equation

HRID 2359700 reaction equation
P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.Br[C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=3)[N:26]=[CH:25][CH:24]=2)[OH:22])=[CH:17][CH:16]=1.[Li+].C[Si]([N-:40][Si](C)(C)C)(C)C>C1(C)C=CC=CC=1.CO.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]>[NH2:40][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=3)[N:26]=[CH:25][CH:24]=2)[OH:22])=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2733832Lithium HexamethyldisilazideHCID 59598381HCID 59598381, compound

Product 1

HCID 59427360HCID 59427360, compoundYield 54.4%

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In a 25 mL sealed tube under N2, were dissolved Pd2(dba)3 (84 mg, 92 μmol), t-Bu3P (1M in PhMe) (92 μl, 92 μmol), (4-bromophenyl)(7-methoxyquinolin-4-yl)methanol (316 mg, 918 μmol) and LiHMDS (1M in THF) (2.75 mL, 2.75 mmol) in 3.5 mL of toluene and the solution was then heated at 80° C. After 3 h, the crude reaction mixture was neutralized by adding 5 drops of MeOH and then directly purified by MPLC (ISCO, dichloromethane:MeOH 100:0 to 90:10) to afford (4-aminophenyl)(7-methoxyquinolin-4-yl)methanol (140 mg, 54% yield). MS (ESI pos. ion) m/z: 281 (MH+). Calc'd exact mass for C17H16N2O2: 280.

Workup

  1. customIn a 25 mL sealed tube under N2
  2. customthe crude reaction mixture
  3. customdirectly purified by MPLC (ISCO, dichloromethane:MeOH 100:0 to 90:10)

Sources & evidence

ORD record
ord-a978026d37174f24b94cb7ea6723dd07
Source dataset
uspto-grants-2014_04
Patent number
US08685983B2

Reaction notes

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