2-Methylpyridine-5-boronic acid → (S)-3-(2-amino-4'-fluoro-2'-(6-methylpyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthene]-7'-yloxy)-2,2-dimethylpropanenitrile

HRID 335997Notes

Reaction equation

HRID 335997 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([N:22]=1)[C:18]1[CH:17]=[C:16](Br)[CH:15]=[C:14]([F:20])[C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([OH:21])=[CH:9][CH:10]=1.CC1C=CC(S(O[CH2:34][C:35]([C:38]#[N:39])([CH3:37])[CH3:36])(=O)=O)=CC=1.[CH3:40][C:41]1[N:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=1>>[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([N:22]=1)[C:18]1[CH:17]=[C:16]([C:44]3[CH:45]=[N:46][C:41]([CH3:40])=[CH:42][CH:43]=3)[CH:15]=[C:14]([F:20])[C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([O:21][CH2:37][C:35]([CH3:34])([CH3:36])[C:38]#[N:39])=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 27630812-Methylpyridine-5-boronic acidHCID 252194682-Cyano-2-methylpropyl 4-methylbenzenesulfonateHCID 67383727(S)-2-amino-2'-bromo-4'-fluoro-5H-spiro[oxazole-4,9'-xanthen]-7'-ol

Product 1

HCID 67387392(S)-3-(2-amino-4'-fluoro-2'-(6-methylpyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthene]-7'-yloxy)-2,2-dimethylpropanenitrile

Procedure

The titled compound was synthesized by steps analogous to those described in method AA13 above, but using (S)-2-amino-2′-bromo-4′-fluoro-5H-spiro[oxazole-4,9′-xanthen]-7′-ol (prepared as described in Method BB40 but using 4-bromo-2-fluorophenol and 2-bromo-5-methoxybenzoic acid), 2-cyano-2-methylpropyl 4-methylbenzenesulfonate, and (6-methylpyridin-3-yl)boronic acid.

Sources & evidence

ORD record
ord-919c517ce6514c8cb5daa89bcbe8424a
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

Loading…