3-Fluorophenylboronic acid → (S)-3-(5'-amino-7-(3-fluorophenyl)-2',6'-dihydro spiro[chromeno[2,3-c]pyridine-5,3'-[1,4]oxazine]-3-yloxy)-2,2-dimethylpropanenitrile

HRID 1472480Notes

Reaction equation

HRID 1472480 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@:15]3([N:20]=[C:19]([NH2:21])[CH2:18][O:17][CH2:16]3)[C:14]3[CH:13]=[C:12](Cl)[N:11]=[CH:10][C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[OH:23][CH2:24][C:25]([CH3:29])([CH3:28])[C:26]#[N:27].[F:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1>>[NH2:21][C:19]1[CH2:18][O:17][CH2:16][C@:15]2([C:14]3[CH:13]=[C:12]([O:23][CH2:24][C:25]([CH3:29])([CH3:28])[C:26]#[N:27])[N:11]=[CH:10][C:9]=3[O:8][C:5]3[C:4]2=[CH:3][C:2]([C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([F:30])[CH:36]=2)=[CH:7][CH:6]=3)[N:20]=1

Participants

4

Reactant 3

HCID 27339863-Fluorophenylboronic acidHCID 135313833-Hydroxy-2,2-dimethylpropanenitrileHCID 58465879(S)-7-bromo-3-chloro-2',6'-dihydrospiro[chromeno [2,3-c]pyridine-5,3'-[1,4]oxazin]-5'-amine

Product 1

HCID 58465895(S)-3-(5'-amino-7-(3-fluorophenyl)-2',6'-dihydro spiro[chromeno[2,3-c]pyridine-5,3'-[1,4]oxazine]-3-yloxy)-2,2-dimethylpropanenitrile

Procedure

The title compound was synthesized by steps analogous to those described in Method A4, but using Intermediate 10B, 3-hydroxy-2,2-dimethylpropanenitrile, and 3-fluorophenylboronic acid. MS m/z=459.3 [M+H]+. Calculated for C26H23FN4O3: 458.18.

Sources & evidence

ORD record
ord-9d3201fdc04f44fa8c375e623bad5257
Source dataset
uspto-grants-2015_04
Patent number
US09012446B2

Reaction notes

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