2-Fluoropyridine-3-boronic acid → (S)-7-(2-fluoropyridin-3-yl)-3-(2-fluoropyridin-4-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-thiazol]-2'-amine

HRID 336014Notes

Reaction equation

HRID 336014 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C@@:15]3([CH2:19][S:18][C:17]([NH2:20])=[N: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.[F:22][C:23]1[C:28](B(O)O)=[CH:27][CH:26]=[CH:25][N:24]=1.[F:32][C:33]1[CH:38]=[C:37](B(O)O)[CH:36]=[CH:35][N:34]=1>>[F:22][C:23]1[C:28]([C:2]2[CH:3]=[C:4]3[C@@:15]4([CH2:19][S:18][C:17]([NH2:20])=[N:16]4)[C:14]4[CH:13]=[C:12]([C:37]5[CH:36]=[CH:35][N:34]=[C:33]([F:32])[CH:38]=5)[N:11]=[CH:10][C:9]=4[O:8][C:5]3=[CH:6][CH:7]=2)=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

4

Reactant 3

HCID 27832702-Fluoropyridine-3-boronic acidHCID 27833962-Fluoropyridine-4-boronic acidHCID 58466138(S)-7-bromo-3-chloro-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-thiazol]-2'-amine

Product 1

HCID 53464569(S)-7-(2-fluoropyridin-3-yl)-3-(2-fluoropyridin-4-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-thiazol]-2'-amine

Procedure

The titled compound was synthesized by steps analogous to those described in method BB12 above, but using (S)-7-bromo-3-chloro-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-thiazol]-2′-amine (prepared as described in Method BB26 but using 7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one), 2-fluoropyridin-3-ylboronic acid and 2-fluoropyridin-4-ylboronic acid.

Sources & evidence

ORD record
ord-4ff6ff5bb80040a9bf825e1d3d5f120a
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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