Potassium Fluoride → HCID 67197500, compound

HRID 544914Notes

Reaction equation

HRID 544914 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH3:17])[N:10]([C@@H:18]3[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[C@@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:19]3[O:20][C:21](=[O:23])[CH3:22])[CH:9]=2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1)CCC.[F-].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Cu]I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:17][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[C:8]([CH2:7][C:5]1[S:6][C:2]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=3)=[CH:3][CH:4]=1)=[CH:9][N:10]2[C@@H:18]1[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[C@@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:19]1[O:20][C:21](=[O:23])[CH3:22]

Participants

8

Reactant 3

HCID 522689Potassium FluorideHCID 6077842-(Tributylstannyl)pyridineHCID 67199228HCID 67199228, compound

Product 1

HCID 67197500HCID 67197500, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(5-bromothiophen-2-yl-methyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 45-(3) (345 mg), 2-(tri-n-butylstannyl)pyridine (997 mg), copper(I) iodide (20 mg) and tetrakis(triphenylphosphine)-palladium(0) (63 mg) in toluene (10 ml) was refluxed for 3 hours under argon atmosphere. The reaction mixture was diluted with ethyl acetate, and thereto was added a 10% aqueous potassium fluoride solution. The resultant mixture was stirred vigorously, and the insoluble materials were filtered off. The filtrate was separated, and the organic layer was washed with brine and dried over sodium sulfate. The insoluble materials were filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane ethyl acetate=90:10-50:50) to give 4-methyl-3-(5-(2-pyridyl)thiophen-2-yl-methyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole (122 mg) as a pale yellow solid. APCI-Mass m/Z 635 (M+H).

Workup

  1. temperaturewas refluxed for 3 hours under argon atmosphere
  2. filtrationthe insoluble materials were filtered off
  3. customThe filtrate was separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe insoluble materials were filtered off
  7. customthe filtrate was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane ethyl acetate=90:10-50:50)

Sources & evidence

ORD record
ord-7cf8c8d7da3f4035948f519707177f2d
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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