2-Fluoropyridine-3-boronic acid → (S)-4'-fluoro-2'-(2-fluoro-2-methylpropoxy)-7'-(2-fluoropyridin-3-yl)-5H-spiro[thiazole-4,9'-xanthen]-2-amine

HRID 336019Notes

Reaction equation

HRID 336019 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][C@@:5]2([N:22]=1)[C:18]1[CH:17]=[C:16]([OH:19])[CH:15]=[C:14]([F:20])[C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8](Br)=[CH:9][CH:10]=1.[F:23][C:24]1[C:29](B(O)O)=[CH:28][CH:27]=[CH:26][N:25]=1.FC(F)(F)S(O[CH2:39][C:40]([F:43])([CH3:42])[CH3:41])(=O)=O>>[F:20][C:14]1[C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([C:29]4[C:24]([F:23])=[N:25][CH:26]=[CH:27][CH:28]=4)=[CH:9][CH:10]=3)[C@@:5]3([CH2:4][S:3][C:2]([NH2:1])=[N:22]3)[C:18]=2[CH:17]=[C:16]([O:19][CH2:39][C:40]([F:43])([CH3:42])[CH3:41])[CH:15]=1

Participants

4

Reactant 3

HCID 27832702-Fluoropyridine-3-boronic acidHCID 121655342-Fluoro-2-methylpropyl trifluoromethanesulfonateHCID 67383112(S)-2-amino-7'-bromo-4'-fluoro-5H-spiro[thiazole-4,9'-xanthen]-2'-ol

Product 1

HCID 58466216(S)-4'-fluoro-2'-(2-fluoro-2-methylpropoxy)-7'-(2-fluoropyridin-3-yl)-5H-spiro[thiazole-4,9'-xanthen]-2-amine

Procedure

The titled compound was synthesized by steps analogous to those described in method AA14 above, but using (S)-2-amino-7′-bromo-4′-fluoro-5H-spiro[thiazole-4,9′-xanthen]-2′-ol (prepared as described in Method BB26 and Example 2 but using 7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one), 2-fluoropyridin-3-ylboronic acid and 2-fluoro-2-methylpropyl trifluoromethanesulfonate. MS m/z=472.0 [M+H]+.

Sources & evidence

ORD record
ord-15ed850751c24bb9b84533751af5e7a4
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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