Tetrahydrothiopyran-4-one → HCID 9796492, compound

HRID 844237Notes

Reaction equation

HRID 844237 reaction equation
[OH:1][C:2]1([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[CH:13][NH:14]3)=[CH:10][CH:9]=2)[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1.BrC1C=C2C(C=C([CH:27]([NH:29][CH:30]3[CH2:32]C3)C)N2)=CC=1.[Li][CH2:34]CCC.S1CCC(=O)CC1>>[CH3:34][N:29]([CH2:30][CH2:32][N:14]1[C:15]2[C:11](=[CH:10][CH:9]=[C:8]([C:2]3([OH:1])[CH2:7][CH2:6][S:5][CH2:4][CH2:3]3)[CH:16]=2)[CH:12]=[CH:13]1)[CH3:27]

Participants

5

Reactant 4

HCID 66173Tetrahydrothiopyran-4-oneHCID 404251484-(1H-Indol-6-yl)thian-4-olHCID 54251766HCID 54251766, compoundHCID 178418339Butyllithium

Product 1

HCID 9796492HCID 9796492, compound

Procedure

1-(N-Cyclopropylamino)ethyl)-6-(4-hydroxy-tetrahydrothiopyran-4-yl)-1H-indole: (34.2 mg, 8%); from 6-bromo-1-(N-Cyclopropylamino)ethyl indole (400.0 mg, 1.32 mmol), nBuLi (2.5M, 1.32 mL, 3.30 mmol) and tetrahydrothiopyran-4-one (760.0 mg, 6.59 mmol).

Sources & evidence

ORD record
ord-0549684dd1de42bdad5f4113778c760a
Source dataset
uspto-grants-2002_04
Patent number
US06380242B1

Reaction notes

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