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

HRID 336010Notes

Reaction equation

HRID 336010 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.[O:32]1[CH2:37][CH2:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH2:33]1>>[O:32]1[CH2:37][CH2:36][CH:35]=[C:34]([C:12]2[N:11]=[CH:10][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:28]2[C:23]([F:22])=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:7][CH:6]=4)[CH2:33]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 58466138(S)-7-bromo-3-chloro-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-thiazol]-2'-amine

Product 1

HCID 58466270(S)-3-(5,6-dihydro-2H-pyran-3-yl)-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 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-(5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Sources & evidence

ORD record
ord-382d6e8be3ae43fbbc03de2e36eaa111
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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