Tetramethyltin → 2-(S)-(4-Acetoxymethyl-7-methyl-1H-indazol-5-ylmethyl)-succinic acid diethyl ester

HRID 132228Notes

Reaction equation

HRID 132228 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C@@H:5]([CH2:12][C:13]1[C:14]([CH2:23][O:24][C:25](=[O:27])[CH3:26])=[C:15]2[C:19](=[C:20](Br)[CH:21]=1)[NH:18][N:17]=[CH:16]2)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[CH3:29][Sn](C)(C)C>>[CH2:1]([O:3][C:4](=[O:28])[C@@H:5]([CH2:12][C:13]1[C:14]([CH2:23][O:24][C:25](=[O:27])[CH3:26])=[C:15]2[C:19](=[C:20]([CH3:29])[CH:21]=1)[NH:18][N:17]=[CH:16]2)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2]

Participants

3

Reactant 2

HCID 11661TetramethyltinHCID 59731854(S)-Diethyl 2-((4-(acetoxymethyl)-7-bromo-1H-indazol-5-yl)methyl)succinate

Product 1

HCID 597319772-(S)-(4-Acetoxymethyl-7-methyl-1H-indazol-5-ylmethyl)-succinic acid diethyl esterYield 68%

Procedure

2-(S)-(4-Acetoxymethyl-7-bromo-1H-indazol-5-ylmethyl)-succinic acid diethyl ester (350 mg, 0.77 mmol) and tetramethyltin (150 μL, 1.1 mmol) were reacted in a manner analogous to the preparation of [4-Methyl-9-(2,2-dimethyl-propyl)-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-(S)-cyclohepta[e]inden-7-yl]-acetic acid methyl ester. Title compound was obtained as pale yellow solid in 68% yield. MS m/e (M−H)−=389.1.

Sources & evidence

ORD record
ord-03eb0a6c38f64824957f4ab13194ca6c
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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