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

HRID 336025Notes

Reaction equation

HRID 336025 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][CH2:37][CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH2:34]1>>[O:33]1[CH2:38][CH2:37][CH:36]=[C:35]([C:12]2[N:11]=[C:10]([F:22])[C:9]3[O:8][C:5]4[C:4]([C@@:15]5([CH2:19][S:18][C:17]([NH2:20])=[N:16]5)[C:14]=3[CH:13]=2)=[CH:3][C:2]([C:29]2[C:24]([F:23])=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:7][CH:6]=4)[CH2:34]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 86658508(S)-7-bromo-3-chloro-1-fluoro-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-thiazol]-2'-amine

Product 1

HCID 53464449(S)-3-(5,6-dihydro-2H-pyran-3-yl)-1-fluoro-7-(2-fluoropyridin-3-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 AA1 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 2-(5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane MS m/z=464.9 [M+H]+. Calculated for C24H18F2N4O2S: 464.49.

Sources & evidence

ORD record
ord-429d01d9e9c540ecb70eeff07d462eef
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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