Allyl bromide → HCID 23365849, compound

HRID 275169Notes

Reaction equation

HRID 275169 reaction equation
[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([OH:32])=[N:15][N:16]3[CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=3[O:30][CH3:31])=[CH:12][CH:11]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:33](Br)[CH:34]=[CH2:35].[H-].[Na+].C(N1C(=O)C2C(=CC(NC(=O)CC3CCCC3)=CC=2)N1CC1C=CC(C(OC)=O)=CC=1OC)C=C>CN(C)C=O>[CH2:35]([O:32][C:14]1[C:13]2[C:17](=[CH:18][C:10]([NH:9][C:7](=[O:8])[CH2:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:11][CH:12]=2)[N:16]([CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=2[O:30][CH3:31])[N:15]=1)[CH:34]=[CH2:33]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 23365834HCID 23365834, compoundHCID 178497910HCID 178497910, compound

Product 1

HCID 23365849HCID 23365849, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The starting ester methyl 4-[2-allyl-6-(2-cyclopentylacetamido)-3-oxo-2H,3H-indazol-1-ylmethyl]-3-methoxybenzoate was itself prepared as follows. Using a similar procedure to that described in Example 42, except starting from methyl 4-[6-(2-cyclopentylacetamido)-3-hydroxyindazol-1-ylmethyl]-3-methoxybenzoate (that is, reaction of this compound with allyl bromide in N,N-dimethylformamide in the presence of sodium hydride), a mixture of methyl 4-[2-allyl-6-(2-cyclopentylacetamido)-3-oxo-2H,3H-indazol-1-ylmethyl]-3-methoxybenzoate, and methyl 4-[3-allyloxy-6-(2-cyclopentylacetamido)indazol-1-ylmethyl]-3-methoxybenzoate was obtained. The mixture of compounds was heated neat at 200° C. for 18 hours, and the product isolated by flash chromatography on silica gel (60 g.), eluting with 1:30:70 v/v/v acetic acid:ethyl acetate:dichloromethane, to give methyl 4-[2-allyl-6-(2-cyclopentylacetamido)-3-oxo-2H,3H-indazol-1-ylmethyl]-3-methoxybenzoate in 81% yield, as an oil with satisfactory NMR spectral data.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-1b77104404a3414d9d4cbf8cd091c61d
Source dataset
uspto-grants-1995_02
Patent number
US05391758

Reaction notes

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