Lithium diisopropylamide → 6-Cyano-1-fluoro-1-(5-isothiazolyl)-1,2,3,4-tetrahydronaphthalene

HRID 5937Notes

Reaction equation

HRID 5937 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]1[S:17][N:16]=[CH:15][CH:14]=1)[CH2:8][CH2:7][CH2:6]2)#[N:2].C([N-]C(C)C)(C)C.[Li+].[F:26]N1C(C)(C)C2C=CC=CC=2S1(=O)=O>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([F:26])([C:13]1[S:17][N:16]=[CH:15][CH:14]=1)[CH2:8][CH2:7][CH2:6]2)#[N:2]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 51409122-Fluoro-3,3-dimethyl-2,3-dihydro-1,2-benzisothiazole 1,1-dioxideHCID 189490196-Cyano-1-(5-isothiazolyl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 189490226-Cyano-1-fluoro-1-(5-isothiazolyl)-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Cyano-1-(5-isothiazolyl)-1,2,3,4-tetrahydronaphthalene (Example 26) is converted into the carbanion by treatment with lithium diisopropylamide in THF at -78° and then reacted with N-fluoro-3,3-dimethyl-2,3-dihydro-1,2-benzothiazole-1,1-dioxide. The reaction mixture is allowed to warm to room temperature and is worked up in aqueous medium, yielding the title compound.

Sources & evidence

ORD record
ord-8cd34d005b784e35943429391df8f304
Source dataset
uspto-grants-1993_09
Patent number
US05246952

Reaction notes

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