Iodoethane → HCID 11690710, compound

HRID 898276Notes

Reaction equation

C(=O)(OCC)[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Br:22])[CH:20]=3)[NH:15][C:14](=[O:23])[C@@H:13]2[CH2:24][CH3:25])(=[O:11])=[O:10])=[CH:5][CH:4]=1.I[CH2:31][CH3:32].C([C@@H]1N(S(C2C=CC(O)=CC=2)(=O)=O)C2C(=CC=C(F)C=2)N(CCC)C1=O)C>>[Br:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:31][CH3:32])[C:14](=[O:23])[C@H:13]([CH2:24][CH3:25])[N:12]2[S:9]([C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=1)(=[O:11])=[O:10]

Participants

Reactant 3

HCID 6340Iodoethane

HCID 11538398(3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-3,4-dihydroquinoxalin-2(1H)-one

HCID 69221446HCID 69221446, compound

Product 1

HCID 11690710HCID 11690710, compound

Procedure

4-{[(2S)-7-Bromo-2-ethyl-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl ethyl carbonate was treated with iodoethane 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)-6-bromo-1,3-diethyl-4-[(4-hydroxyphenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one. [α]D25=−190° (c=0.0052 G/ML, DMSO); MS (ESI) m/z 439/441 ([M+H]+); MS (ESI) m/z 437/439 ([M−H]−); Anal. Calcd for C18H19BrN2O4S: C, 49.21; H, 4.36; N, 6.38. Found: C, 50.41; H, 5.02; N, 6.00.

Sources & evidence

ORD record: ord-ddc0387bb9d54d028c3a28251b1733e0
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351709B2

Reaction notes

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