2-Fluoropyridine-3-boronic acid → (S)-3-(5,6-dihydro-2H-pyran-3-yl)-1-fluoro-7-(2-fluoropyridin-3-yl)-5',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,4'-[1,3]oxazin]-2'-amine

HRID 1472459Notes

Reaction equation

HRID 1472459 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.[O:34]1[CH2:39][CH2:38][CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH2:35]1>>[O:34]1[CH2:39][CH2:38][CH:37]=[C:36]([C:12]2[N:11]=[C:10]([F:23])[C:9]3[O:8][C:5]4[C:4]([C@@:15]5([CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]5)[C:14]=3[CH:13]=2)=[CH:3][C:2]([C:30]2[C:25]([F:24])=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:7][CH:6]=4)[CH2:35]1

Participants

4

Reactant 3

HCID 27832702-Fluoropyridine-3-boronic acidHCID 158366332-(5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 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 53373856(S)-3-(5,6-dihydro-2H-pyran-3-yl)-1-fluoro-7-(2-fluoropyridin-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 2-(5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Sources & evidence

ORD record
ord-e6329472429d4c8f9b45ad1b4f9317cc
Source dataset
uspto-grants-2015_04
Patent number
US09012446B2

Reaction notes

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