5-Fluoroindoline → HCID 69837952, compound

HRID 352366Notes

Reaction equation

HRID 352366 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](Br)[CH:11]=2)[CH2:6][CH2:5]1)(=O)C.FC1C=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH2:20][CH2:19]2.C[C@H]1N[C@@H](C)C[NH:28][CH2:27]1>>[F:14][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[N:21]1[CH2:20][C@H:19]([CH3:18])[N:28]([CH3:27])[C@H:23]([CH3:24])[CH2:22]1)[NH:4][CH2:5][CH2:6]2

Participants

4

Reactant 3

HCID 27744635-FluoroindolineHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 21948372HCID 21948372, compound

Product 1

HCID 69837952HCID 69837952, compound

Procedure

The title compound was prepared from 1-acetyl-6-bromo-5-fluoroindoline (prepared by bromination of 5-fluoroindoline analogous to procedure in J. Het. Chem. 1983, 20, 349, followed by N-acylation) by reaction with cis-3,5-dimethylpiperazine using similar procedure to Description 2 (82%), followed by N-methylation using procedure similar to Description 24 (69%), followed by hydrolysis as in Description 3 (96%). The product was isolated as a pale yellow solid.

Workup

  1. customThe product was isolated as a pale yellow solid

Sources & evidence

ORD record
ord-d3f916cb8c604131afa16fcf8d515c03
Source dataset
uspto-grants-2004_06
Patent number
US06747030B1

Reaction notes

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