HCID 15840342, compound → HCID 86756142, compound

HRID 1935638Notes

Reaction equation

HRID 1935638 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:16]1[O:20][C:19]([CH:21]2[O:26][CH2:25][CH2:24]C[O:22]2)=[CH:18][CH:17]=1)CCC>CN(C=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>[O:26]1[CH2:25][CH2:24][O:22][CH:21]1[C:19]1[O:20][C:16]([N:3]2[CH:2]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]3)=[N:4]2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 15840342HCID 15840342, compoundHCID 178506566HCID 178506566, compound

Product 1

HCID 86756142HCID 86756142, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

10 g (41 mmol) of 3-iodoindazole (U. Wrzeciono et al., Pharmazie 1979, 34, 20) are dissolved in 125 ml of DMF under argon, 0.7 g of Pd(PPh3)4 is added and the mixture is stirred for 15 minutes. 19.4 g (43.9 mmol) of 2-(5-tributylstannyl-2-furanyl)-1,3-dioxane are added and the mixture is stirred at 100° C. for 2 hours. The solvent is evaporated off in vacuo and the residue is chromatographed over silica gel using toluene and toluene/ethyl acetate mixtures as the eluent. 10 g (90.3% of theory) of 3-(2-(5-(1,3-dioxolan-2-yl)furyl)indazole are obtained.

Workup

  1. stirringthe mixture is stirred at 100° C. for 2 hours
  2. customThe solvent is evaporated off in vacuo
  3. customthe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-f4c9e6654bfd485b9bc31ffd165a6a99
Source dataset
uspto-grants-2002_05
Patent number
US06387940B1

Reaction notes

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