2-Fluoropyridine-3-boronic acid → (S)-4'-fluoro-2'-(2-fluoro-2-methylpropoxy)-7'-(2-fluoropyridin-3-yl)-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthen]-2-amine

HRID 455740Notes

Reaction equation

HRID 455740 reaction equation
Br[C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:24])=[CH:9][C:10]([O:22][CH3:23])=[CH:11][C:12]=3[C@@:13]32[CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]3)=[CH:4][CH:3]=1.[F:25][C:26]1[C:31](B(O)O)=[CH:30][CH:29]=[CH:28][N:27]=1.FC(F)(F)S(O[CH2:41][C:42]([F:45])(C)[CH3:43])(=O)=O>>[F:24][C:8]1[C:7]2[O:6][C:5]3[C:14](=[CH:15][C:2]([C:31]4[C:26]([F:25])=[N:27][CH:28]=[CH:29][CH:30]=4)=[CH:3][CH:4]=3)[C@@:13]3([CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]3)[C:12]=2[CH:11]=[C:10]([O:22][CH2:23][C:42]([F:45])([CH3:43])[CH3:41])[CH:9]=1

Participants

4

Reactant 3

HCID 27832702-Fluoropyridine-3-boronic acidHCID 121655342-Fluoro-2-methylpropyl trifluoromethanesulfonateHCID 58465963(S)-7'-bromo-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthen]-2-amine

Product 1

HCID 58465950(S)-4'-fluoro-2'-(2-fluoro-2-methylpropoxy)-7'-(2-fluoropyridin-3-yl)-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthen]-2-amine

Procedure

The title compound was synthesized by steps analogous to those described in method A8 above, but using intermediate 20B, 2-fluoropyridin-3-ylboronic acid and 2-fluoro-2-methylpropyl trifluoromethanesulfonate.

Sources & evidence

ORD record
ord-f3e37f39a1aa4795a88efc52f5fbcfc0
Source dataset
uspto-grants-2013_07
Patent number
US08497264B2

Reaction notes

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