3-Fluoropyrrolidine → (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 1472471Notes

Reaction equation

HRID 1472471 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.[F:35][C@@H:36]1[CH2:40]CN[CH2:37]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]([O:22][CH2:23][C:36]([F:35])([CH3:40])[CH3:37])[CH:9]=1

Participants

4

Reactant 3

HCID 27591633-FluoropyrrolidineHCID 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 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 A6 above, but using intermediate 20B, 2-fluoropyridin-3-ylboronic acid and (R)-3-fluoropyrrolidine. MS m/z=467.0 [M+H]+. Calculated for C25H21F3N4O2: 466.16

Sources & evidence

ORD record
ord-c850adf6f72541d5a5c94f5dfb7b88c5
Source dataset
uspto-grants-2015_04
Patent number
US09012446B2

Reaction notes

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