Cesium fluoride → 3-(2-methoxymethyl-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole

HRID 1038124Notes

Reaction equation

HRID 1038124 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([Sn](CCCC)(CCCC)CCCC)[CH:7]=[CH:6][N:5]=1.Br[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([N+:33]([O-:35])=[O:34])[CH:31]=2)[N:26]([C:36]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:25]=1.[F-].[Cs+]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([N+:33]([O-:35])=[O:34])[CH:31]=3)[N:26]([C:36]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:25]=2)[CH:7]=[CH:6][N:5]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 589464433-bromo-5-nitro-1-trityl-1H-indazoleHCID 866301802-Methoxymethyl-4-tributylstannanyl-pyridine

Product 1

HCID 866301793-(2-methoxymethyl-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-methoxymethyl-4-tributylstannanyl-pyridine 8AN (0.1 g, 0.24 mmol), 3-bromo-5-nitro-1-trityl-1H-indazole 1AJ (0.12 g, 0.24 mmol), CsF (0.08 g, 0.53 mmol), [Pd2(dba)3] (5 mg, 0.005 mmol), Pd[P(t-Bu)3)2, and CuI (4 mg, 0.024 mmol) in DMF (2 ml) was degassed for 5 minutes. Then it was heated at 120° C. for two hours. Cooled to room temperature and diluted with EtOAc (10 ml). It was then filtered on a celite pad. Filtrate was washed with water (3 ml) and the organic extracts were dried over MgSO4. It was filtered again on a celite pad and concentrated. The residue was purified on silica gel eluting with 2/1 EtOAc/Hexane to give the desired product 3-(2-methoxymethyl-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole 9AN (0.095 g, 76%).

Workup

  1. customwas degassed for 5 minutes
  2. temperatureCooled to room temperature
  3. additiondiluted with EtOAc (10 ml)
  4. filtrationIt was then filtered on a celite pad
  5. washFiltrate was washed with water (3 ml)
  6. dry with materialthe organic extracts were dried over MgSO4
  7. filtrationIt was filtered again on a celite pad
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel eluting with 2/1 EtOAc/Hexane

Sources & evidence

ORD record
ord-961440aad37c4965b2e1a5e5ee05bae6
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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