3-Pyridinylboronic acid → (S)-1-fluoro-7-(2-fluoropyridin-3-yl)-3-(pyridin-3-yl)-5',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,4'-[1,3]oxazin]-2'-amine

HRID 1472462Notes

Reaction equation

HRID 1472462 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:15]3([CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]3)[C:14]3[CH:13]=[C:12](Cl)[N:11]=[C:10]([F:23])[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[F:24][C:25]1[C:30](B(O)O)=[CH:29][CH:28]=[CH:27][N:26]=1.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36](B(O)O)[CH:35]=1>>[F:23][C:10]1[C:9]2[O:8][C:5]3[C:4]([C@@:15]4([CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]4)[C:14]=2[CH:13]=[C:12]([C:36]2[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=2)[N:11]=1)=[CH:3][C:2]([C:30]1[C:25]([F:24])=[N:26][CH:27]=[CH:28][CH:29]=1)=[CH:7][CH:6]=3

Participants

4

Reactant 3

HCID 27343783-Pyridinylboronic acidHCID 27832702-Fluoropyridine-3-boronic acidHCID 58465925(S)-7-bromo-3-chloro-1-fluoro-5',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,4'-[1,3]oxazin]-2'-amine

Product 1

HCID 58465983(S)-1-fluoro-7-(2-fluoropyridin-3-yl)-3-(pyridin-3-yl)-5',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,4'-[1,3]oxazin]-2'-amine

Procedure

The title compound was synthesized by steps analogous to those described in method A1 above, but using intermediate 15B, 2-fluoropyridin-3-ylboronic acid and 3-pyridylboronic acid. MS m/z=458.0 [M+H]+. Calculated for C25H17F2N5O2: 457.14

Sources & evidence

ORD record
ord-263899542d0349a3990169a2fe0bfa64
Source dataset
uspto-grants-2015_04
Patent number
US09012446B2

Reaction notes

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