3-Pyridinylboronic acid → (S)-3-(2-fluoropyridin-4-yl)-1-methoxy-7-(pyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

HRID 336018Notes

Reaction equation

HRID 336018 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:15]3([CH2:19][O:18][C:17]([NH2:20])=[N:16]3)[C:14]3[CH:13]=[C:12](Cl)[N:11]=[C:10]([O:22][CH3:23])[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[CH:25]=1.[F:33][C:34]1[CH:39]=[C:38](B(O)O)[CH:37]=[CH:36][N:35]=1>>[F:33][C:34]1[CH:39]=[C:38]([C:12]2[N:11]=[C:10]([O:22][CH3:23])[C:9]3[O:8][C:5]4[C:4]([C@@:15]5([CH2:19][O:18][C:17]([NH2:20])=[N:16]5)[C:14]=3[CH:13]=2)=[CH:3][C:2]([C:26]2[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=2)=[CH:7][CH:6]=4)[CH:37]=[CH:36][N:35]=1

Participants

4

Reactant 3

HCID 27343783-Pyridinylboronic acidHCID 27833962-Fluoropyridine-4-boronic acidHCID 58466132(S)-7-bromo-3-chloro-1-methoxy-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

Product 1

HCID 53465209(S)-3-(2-fluoropyridin-4-yl)-1-methoxy-7-(pyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

Procedure

The titled compound was synthesized by steps analogous to those described in method AA1 above, but using (S)-7-bromo-3-chloro-1-methoxy-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (prepared as described in Method CC16), pyridin-3-ylboronic acid and 2-fluoropyridin-4-ylboronic acid.

Sources & evidence

ORD record
ord-a796cdfb7e3c48efa56ff203f652733c
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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