Methanesulfonyl chloride → 3-{4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]butyl}-5-fluoroindole, hydrochloride

HRID 1068688Notes

Reaction equation

HRID 1068688 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[NH:12][CH:11]=1)(=O)=O.FC1C=C2C(=CC=1)NC=C2CCCCO.[H-].[Al+3].[Li+].[H-].[H-].[H-].FC1C=C2C(=CC=1)NC=C2CCCC(O)=O.CS([Cl:61])(=O)=O.Cl.[O:63]=[C:64]1[CH:69]=[CH:68][C:67]2[CH:70]=[C:71]([N:74]3[CH2:79][CH2:78][NH:77][CH2:76][CH2:75]3)[CH:72]=[CH:73][C:66]=2[O:65]1>C1COCC1.C(N(CC)CC)C.C(#N)C>[ClH:61].[O:63]=[C:64]1[CH:69]=[CH:68][C:67]2[CH:70]=[C:71]([N:74]3[CH2:75][CH2:76][N:77]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]4[C:18]5[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=5)[NH:12][CH:11]=4)[CH2:78][CH2:79]3)[CH:72]=[CH:73][C:66]=2[O:65]1

Participants

10

Reactant 6

HCID 31297Methanesulfonyl chlorideHCID 111088894-(5-Fluoroindol-3-yl)butyl methanesulfonateHCID 150472684-(5-Fluoro-1H-indol-3-yl)butanoic acidHCID 183302714-(5-fluoro-1H-indol-3-yl)butan-1-olHCID 21226445Aluminium lithium hydrideHCID 1317227094-(2-oxo-2H-1-benzopyran-6-yl)piperazine, hydrochloride

Product 1

HCID 111785583-{4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]butyl}-5-fluoroindole, hydrochloride

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 5.10 g (0.017 mol) of 4-(5-fluoroindol-3-yl)butyl methanesulfonate [obtainable by reaction of 4-(5-fluoroindol-3-yl)butanol (obtainable by lithium aluminium hydride reduction of 4-(5-fluoroindol-3-yl)butanoic acid, which can be prepared analogously to a Japp-Klingemann reaction, in THF) with methanesulfonyl chloride], 4.0 g (0.015 mol) of 4-(2-oxo-2H-1-benzopyran-6-yl)piperazine, hydrochloride (obtainable as described in Example 1), 200 ml of acetonitrile and 10.0 ml of triethylamine is reacted for 30 hours on a steam bath with stirring. After customary working up, 3-{4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]butyl}-5-fluoroindole, hydrochloride, m.p. 293-295°, is obtained.

Workup

  1. customis reacted for 30 hours on a steam bath

Sources & evidence

ORD record
ord-a1ba928dcce741318c149cd8af38cedd
Source dataset
uspto-grants-2001_06
Patent number
US06251908B1

Reaction notes

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