Tetrahydrofuran → HCID 67184252, compound

HRID 1183117Notes

Reaction equation

HRID 1183117 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]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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 178418397HCID 178418397, compoundCatalyst

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(0) (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-c7e021fe32f94486af2a4903d4ba600d
Source dataset
uspto-grants-2014_03
Patent number
US08664242B2

Reaction notes

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