Water → 3-(5-(1,3-Dioxan-2-yl)furan-2-yl)-1-(4-picolyl)indazole

HRID 2227550Notes

Reaction equation

HRID 2227550 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[O:11][C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][N:13]=2)=[CH:9][CH:8]=1.[H-].[Na+].Cl.[N:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][CH:25]=1.O>CN(C=O)C.C(OCC)(=O)C>[O:3]1[CH2:4][CH2:5][CH2:6][O:1][CH:2]1[C:7]1[O:11][C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:30][C:27]3[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=3)[N:13]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 745704-(Chloromethyl)pyridinium chlorideHCID 15840328HCID 15840328, compound

Product 1

HCID 158403293-(5-(1,3-Dioxan-2-yl)furan-2-yl)-1-(4-picolyl)indazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2 g (7.41 mmol) of 3-(5-(1,3-dioxan-2-yl)furan-2-yl)indazole in 10 ml of DMF is added to a suspension of 355 mg of NaH (60 per cent in paraffin) in 10 ml of DMF under argon, and the mixture is stirred at room temperature for 1 hour. 1.46 g of 4-picolyl chloride hydrochloride are then added, followed by 355 mg of NaH (60 percent in paraffin). The mixture is stirred at room temperature for 1 hour and then at 100° C. for 1 hour, introduced into water and extracted with ethyl acetate, the organic phase is dried with sodium sulphate and evaporated in vacuo and the residue is chromatographed over silica gel using toluene/ethyl acetate mixtures as the eluent. 1 g (37% of theory) of an oil is obtained. Rf (SiO2, ethyl acetate): 0.25

Workup

  1. stirringThe mixture is stirred at room temperature for 1 hour
  2. waitat 100° C. for 1 hour
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic phase is dried with sodium sulphate
  5. customevaporated in vacuo
  6. customthe residue is chromatographed over silica gel
  7. custom1 g (37% of theory) of an oil is obtained

Sources & evidence

ORD record
ord-940541aad2f5400c9cce69dd8fb58bce
Source dataset
uspto-grants-2002_07
Patent number
US06414009B1

Reaction notes

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