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

HRID 1472476Notes

Reaction equation

HRID 1472476 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](OC)=[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.[N:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1>>[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]([C:38]2[CH:39]=[CH:40][N:35]=[CH:36][CH:37]=2)[CH:9]=1

Participants

4

Reactant 3

HCID 2734379(Pyridin-4-yl)boronic acidHCID 27832702-Fluoropyridine-3-boronic acidHCID 58465963(S)-7'-bromo-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthen]-2-amine

Product 1

HCID 58465953(S)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2'-(pyridin-4-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 A7 above, but using intermediate 20B, 2-fluoropyridin-3-ylboronic acid and 4-pyridineboronic acid. MS m/z=456.8 [M+H]+. Calculated for C26H18F2N4O2: 456.14

Sources & evidence

ORD record
ord-e65684cf54a946e5b601b10f8230f33d
Source dataset
uspto-grants-2015_04
Patent number
US09012446B2

Reaction notes

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