Tetrahydrofuran → HCID 67184252, compound

HRID 1423288Notes

Reaction equation

HRID 1423288 reaction equation
[C:1]1(NS(C(F)(F)F)(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]([N:18]([CH3:20])C)=O.[CH2:21]([O:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:38](=O)([O-])[O-].[K+].[K+].[CH2:44]1[CH2:48]O[CH2:46][CH2:45]1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH2:20]([N:18]1[CH:16]2[CH2:15][CH2:48][CH:44]1[CH:45]=[C:46]([C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([O:28][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:30]=1)[CH2:38]2)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 27343133-Benzyloxy-phenylboronic acid

Product 1

HCID 67184252HCID 67184252, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

To a solution of the product of the previous step (24.6 g, contaminated with PhNHTf) in THF (120 mL) and DMA (120 mL) at room temperature was added 3-benzyloxyphenylboronic acid (16.46 g), potassium carbonate (19.9 g) and tetrakis(triphenylphosphine)palladium(O) (5.0 g). The resulting mixture was degassed, flushed with nitrogen and then stirred under nitrogen atmosphere overnight. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated to give a dark thick oil which was purified by flash chromatography (and eluted with 40% ethyl acetate in hexanes) to yield the title intermediate (6.9 g). (m/z): [M+H]+ calcd for C27H27NO 382.22; found 382.5.

Workup

  1. customThe resulting mixture was degassed
  2. customflushed with nitrogen
  3. filtrationThe reaction mixture was filtered through a pad of Celite
  4. concentrationthe filtrate was concentrated
  5. customto give a dark thick oil which
  6. customwas purified by flash chromatography (and eluted with 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5589b7c576684e7291fe947046ed23bd
Source dataset
uspto-grants-2015_01
Patent number
US08927573B2

Reaction notes

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