2-Fluoropyridine-3-boronic acid → (S)-1-fluoro-7-(2-fluoropyridin-3-yl)-3-(tetrahydro-2H-pyran-4-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-thiazol]-2'-amine

HRID 336026Notes

Reaction equation

HRID 336026 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]=[C:10]([F:22])[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[F:23][C:24]1[C:29](B(O)O)=[CH:28][CH:27]=[CH:26][N:25]=1.[O:33]1[CH2:38][CH:37]=[C:36](B(O)O)[CH2:35][CH2:34]1>>[F:22][C:10]1[C:9]2[O:8][C:5]3[C:4]([C@@:15]4([CH2:19][S:18][C:17]([NH2:20])=[N:16]4)[C:14]=2[CH:13]=[C:12]([CH:36]2[CH2:37][CH2:38][O:33][CH2:34][CH2:35]2)[N:11]=1)=[CH:3][C:2]([C:29]1[C:24]([F:23])=[N:25][CH:26]=[CH:27][CH:28]=1)=[CH:7][CH:6]=3

Participants

4

Reactant 3

HCID 27832702-Fluoropyridine-3-boronic acidHCID 235936383,6-Dihydro-2H-pyran-4-ylboronic acidHCID 86658508(S)-7-bromo-3-chloro-1-fluoro-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-thiazol]-2'-amine

Product 1

HCID 53464320(S)-1-fluoro-7-(2-fluoropyridin-3-yl)-3-(tetrahydro-2H-pyran-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 AA11 above, but using (S)-7-bromo-3-chloro-1-fluoro-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-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one), 2-fluoropyridin-3-ylboronic acid and 3,6-dihydro-2H-pyran-4-ylboronic acid MS m/z=467.0 [M+H]+. Calculated for C24H20F2N4O2S: 466.50.

Sources & evidence

ORD record
ord-161b58a2c2774f58a53937a820a475d4
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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