Tetrahydrofuran → HCID 86622718, compound

HRID 1673215Notes

Reaction equation

HRID 1673215 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[O:14][C:15]([CH3:20])([CH3:19])[CH2:16][C:17](=[O:18])[C:11]2=[CH:10][C:9]=1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.C1(N[S:50]([C:53]([F:56])([F:55])[F:54])(=[O:52])=[O:51])C=CC=CC=1>CN(C=O)C>[F:54][C:53]([F:56])([F:55])[S:50]([O:18][C:17]1[C:11]2[C:12](=[N:13][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[C:9]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)[CH:10]=2)[O:14][C:15]([CH3:20])([CH3:19])[CH:16]=1)(=[O:52])=[O:51]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 2733832Lithium HexamethyldisilazideHCID 24995912HCID 24995912, compound

Product 1

HCID 86622718HCID 86622718, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the product of Example 3 (0.47 g, 1.2 mmol) in DMF (9 mL) at −78° C., was added 1 M LiHMDS in THF (1.3 mL, 1.3 mmol) and the reaction was stirred for 5 min. N-phenyl trifluoromethanesulfonamide (0.47 g, 1.3 mmol) was added and the reaction was allowed to come to rt. The reaction was stirred an additional 15 min, concentrated and the residue was purified by flash chromatography on silica gel gradient eluted with 0-20% EtOAc in hexane to afford the title compound. Step B: 7-(2-Chlorophenyl)-6-(4-chlorophenyl)-2,2-dimethyl-4-pyridin-4-yl-2H-pyrano[2,3-b]pyridine

Workup

  1. customto come to rt
  2. stirringThe reaction was stirred an additional 15 min
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography on silica gel gradient
  5. washeluted with 0-20% EtOAc in hexane

Sources & evidence

ORD record
ord-a4b76b29b1c44f7594f8ced6c51d6a10
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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