Allyl bromide → (3S)-1-allyl-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one

HRID 898256Notes

Reaction equation

HRID 898256 reaction equation
C(=O)([O-])OC1C=CC(S(N2C3C(=CC=C(F)C=3)NC(=O)[C@@H]2CC)(=O)=O)=CC=1.C(Br)C=C.[CH2:32]([C@@H:34]1[N:43]([S:44]([C:47]2[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([F:54])[CH:41]=2)[N:36]([CH2:55][CH2:56][CH3:57])[C:35]1=[O:58])[CH3:33]>>[CH2:55]([N:36]1[C:37]2[C:42](=[CH:41][C:40]([F:54])=[CH:39][CH:38]=2)[N:43]([S:44]([C:47]2[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[C@@H:34]([CH2:32][CH3:33])[C:35]1=[O:58])[CH:56]=[CH2:57]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 11538398(3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 866027294-{[(2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate

Product 1

HCID 11625290(3S)-1-allyl-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one

Procedure

4-{[(2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxalin-1 (2H)-yl]sulfonyl}phenyl carbonate (see Example 20) was treated with allyl bromide according to the procedure for the preparation of (3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-3,4-dihydroquinoxalin-2(1H)-one (see Example 20) to yield (3S)-1-allyl-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one. [α]D25=−20° (c=0.005 G/ML, DMSO); MS (ESI) m/z 391 ([M+H]+); MS (ESI) m/z 389 ([M−H]−); Anal. Calcd for C19H19FN2O4S: C, 58.45; H, 4.91; N, 7.17. Found: C, 54.53; H, 4.50; N, 6.22.

Sources & evidence

ORD record
ord-809ef2c791224b0684ae65377287e38c
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

Loading…