4-Iodo-2-methylphenol → HCID 67341414, compound

HRID 1673288Notes

Reaction equation

HRID 1673288 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([O:12][C@@H:13]1[O:39][C@H:38]([CH2:40][O:41][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[C@@H:30]([O:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[C@H:22]([O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C@H:14]1[O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:6][NH:7]2)#[CH:2].I[C:49]1[CH:54]=[CH:53][C:52]([OH:55])=[C:51]([CH3:56])[CH:50]=1>C(N(CC)CC)C.C(OCC)(=O)C.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.[Cu]I>[OH:55][C:52]1[CH:53]=[CH:54][C:49]([C:2]#[C:1][C:3]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:4]=2[C:5]([O:12][C@@H:13]2[O:39][C@H:38]([CH2:40][O:41][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[C@@H:30]([O:31][C:32](=[O:37])[C:33]([CH3:34])([CH3:35])[CH3:36])[C@H:22]([O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C@H:14]2[O:15][C:16](=[O:21])[C:17]([CH3:18])([CH3:19])[CH3:20])=[N:6][NH:7]3)=[CH:50][C:51]=1[CH3:56]

Participants

7

Reactant 2

HCID 1437134-Iodo-2-methylphenolHCID 86622032HCID 86622032, compound

Product 1

HCID 67341414HCID 67341414, compoundYield 61.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-ethynyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-indazole (66 mg) in triethylamine (1 mL) were added 4-iodo-2-methylphenol (25 mg), tetrakis(triphenylphosphine)palladium (0) (12 mg) and copper (I) iodide (4 mg), and the mixture was stirred at 80° C. under an argon atmosphere overnight. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethylacetate=3/1-2/1-1/1) to give the title compound (47 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe insoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethylacetate=3/1-2/1-1/1)

Sources & evidence

ORD record
ord-cb39498241c54576807e93b30f9b2028
Source dataset
uspto-grants-2011_08
Patent number
US07998975B2

Reaction notes

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