4-(2-Hydroxyethyl)-1lambda~6~,4-thiazinane-1,1-dione → 2-Bromo-3-(2,4-difluorophenyl)-6-[2-(1,1-dioxothiomorpholin-4-yl)ethoxy]-1H-inden-1-one

HRID 331370Notes

Reaction equation

HRID 331370 reaction equation
[Br:1][C:2]1[C:3](=[O:20])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])=[CH:8][CH:7]=[C:6]([OH:19])[CH:5]=2.BrC1C(=O)C2C(C=1C1C=CC=CC=1)=CC=C(O)C=2.[O:39]=[S:40]1(=[O:49])[CH2:45][CH2:44][N:43]([CH2:46][CH2:47]O)[CH2:42][CH2:41]1>>[Br:1][C:2]1[C:3](=[O:20])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])=[CH:8][CH:7]=[C:6]([O:19][CH2:47][CH2:46][N:43]1[CH2:44][CH2:45][S:40](=[O:49])(=[O:39])[CH2:41][CH2:42]1)[CH:5]=2

Participants

4

Reactant 3

HCID 218748114-(2-Hydroxyethyl)-1lambda~6~,4-thiazinane-1,1-dioneHCID 703061762-bromo-6-hydroxy-3-phenyl-1H-inden-1-oneHCID 703074372-Bromo-3-(2,4-difluorophenyl)-6-hydroxy-1H-inden-1-one

Product 1

HCID 703140382-Bromo-3-(2,4-difluorophenyl)-6-[2-(1,1-dioxothiomorpholin-4-yl)ethoxy]-1H-inden-1-oneYield 65%

Procedure

The procedure of Step 6 of Example 1 was repeated except for using 2-bromo-3-(2,4-difluorophenyl)-6-hydroxy-1H-inden-1-one obtained in Step 5 of Example 82 as a starting material instead of 2-bromo-6-hydroxy-3-phenyl-1H-inden-1-one, 2-(1,1-dioxothiomorpholin-4-yl)ethanol instead of 4-(2-hydroxyethyl)morpholine to obtain the title compound (65%).

Sources & evidence

ORD record
ord-fca460f115864247acba9898ba17061e
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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