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

HRID 455743Notes

Reaction equation

HRID 455743 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.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=1.FC(F)(F)S(O[CH2:40][C:41]([F:44])(C)[CH3:42])(=O)=O>>[F:24][C:8]1[C:7]2[O:6][C:5]3[C:14](=[CH:15][C:2]([C:27]4[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=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:41]([F:44])([CH3:42])[CH3:40])[CH:9]=1

Participants

4

Reactant 3

HCID 27343783-Pyridinylboronic 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 58465993(S)-4'-fluoro-2'-(2-fluoro-2-methylpropoxy)-7'-(pyridin-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, pyridin-3-ylboronic acid and 2-fluoro-2-methylpropyl trifluoromethanesulfonate.

Sources & evidence

ORD record
ord-7ef70f37121e4c64a9d75ca39359aecf
Source dataset
uspto-grants-2013_07
Patent number
US08497264B2

Reaction notes

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