Triethylamine → HCID 67341520, compound

HRID 1673303Notes

Reaction equation

HRID 1673303 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:16][N:17]=[C:18]([O:19][C@@H:20]4[O:46][C@H:45]([CH2:47][O:48][C:49](=[O:54])[C:50]([CH3:53])([CH3:52])[CH3:51])[C@@H:37]([O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[C@H:29]([O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C@H:21]4[O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:11]=23)=[CH:4][CH:3]=1.[C:55]([OH:60])(=[O:59])[CH2:56][CH:57]=[CH2:58].C(N(CC)CC)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:55]([CH2:56]/[CH:57]=[CH:58]/[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:16][N:17]=[C:18]([O:19][C@@H:20]4[O:46][C@H:45]([CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:42])([CH3:43])[CH3:41])[C@@H:47]([O:48][C:49](=[O:54])[C:50]([CH3:53])([CH3:52])[CH3:51])[C@H:29]([O:30][C:31](=[O:36])[C:32]([CH3:34])([CH3:33])[CH3:35])[C@H:21]4[O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:25])[CH3:26])[C:11]=23)=[CH:4][CH:3]=1)([OH:60])=[O:59]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 327433-Butenoic acidHCID 80271Tri-o-tolylphosphineHCID 67341446HCID 67341446, compound

Product 1

HCID 67341520HCID 67341520, compoundYield 69.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[2-(4-bromophenyl)ethyl]-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazolo[3,4-b]-pyridine (0.27 g), 3-butenoic acid (56 mg), triethylamine (0.23 mL), palladium (II) acetate (7 mg) and tris(2-methyl-phenyl)phosphine (20 mg) in acetonitrile (5 mL) was heated for reflux under an argon atmosphere overnight. The reaction mixture was diluted with dichloromethane, and the insoluble material was removed by filtration. The filtrate was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1) to give the title compound (0.19 g).

Workup

  1. temperaturewas heated
  2. temperaturefor reflux under an argon atmosphere overnight
  3. customthe insoluble material was removed by filtration
  4. washThe filtrate was washed with 1 mol/L hydrochloric acid, water and brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1)

Sources & evidence

ORD record
ord-89424bbbef4a4d669996f9ae4281fd71
Source dataset
uspto-grants-2011_08
Patent number
US07998975B2

Reaction notes

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