Water → HCID 17751742, compound

HRID 2227557Notes

Reaction equation

HRID 2227557 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[O:10][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)=[CH:8][CH:7]=1.[H-].[Na+].[C:22]([C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Br)#[N:23].O>CN(C=O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:22]([C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([C:9]2[O:10][C:6]([CH:2]3[O:1][CH2:5][CH2:4][O:3]3)=[CH:7][CH:8]=2)=[N:12]1)#[N:23]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 895992-(Bromomethyl)benzonitrileHCID 22239006HCID 22239006, compound

Product 1

HCID 17751742HCID 17751742, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21584019Toluene ethylacetateSolvent

Procedure

A solution of 2 g (7.41 mmol) of 3-(5-(1,3-dioxolan-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. 1.5 g of 2-cyanobenzyl bromide are then added. The mixture is stirred at 100° C. for 30 minutes, 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. 2.1 g (73.5% of theory) of an oil are obtained. Rf(SiO2, toluene/ethyl acetate 1:1): 0.63

Workup

  1. stirringThe mixture is stirred at 100° C. for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase is dried with sodium sulphate
  4. customevaporated in vacuo
  5. customthe residue is chromatographed over silica gel
  6. custom2.1 g (73.5% of theory) of an oil are obtained

Sources & evidence

ORD record
ord-b1939f023bdc4354b9340628701c4c5c
Source dataset
uspto-grants-2002_07
Patent number
US06414009B1

Reaction notes

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