Cesium fluoride → HCID 86630183, compound

HRID 1038126Notes

Reaction equation

HRID 1038126 reaction equation
[CH3:1][O:2][C:3]([C:6]1[CH:11]=[C:10]([Sn](CCCC)(CCCC)CCCC)[CH:9]=[CH:8][N:7]=1)([CH3:5])[CH3:4].Br[C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([N+:35]([O-:37])=[O:36])[CH:33]=2)[N:28]([C:38]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:27]=1.[F-].[Cs+]>CN(C=O)C.CCOC(C)=O.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][C:3]([C:6]1[CH:11]=[C:10]([C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([N+:35]([O-:37])=[O:36])[CH:33]=3)[N:28]([C:38]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[N:27]=2)[CH:9]=[CH:8][N:7]=1)([CH3:4])[CH3:5]

Participants

8

Reactant 3

HCID 25953Cesium fluorideHCID 589464433-bromo-5-nitro-1-trityl-1H-indazoleHCID 866301812-(1-Methoxy-1-methyl-ethyl)-4-tributylstannanyl-pyridine

Product 1

HCID 86630183HCID 86630183, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

2-(1-methoxy-1-methyl-ethyl)-4-tributylstannanyl-pyridine 13AO (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 1/3 EtOAc/Hexane to give the desired product 3-[2-(1-methoxy-1-methyl-ethyl)-pyridin-4-yl]-5-nitro-1-trityl-1H-indazole 14AO (0.05 g, 39%).

Workup

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

Sources & evidence

ORD record
ord-27e4443fef8149b6805da2aa02726018
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

Loading…