(2-Fluoro-4-methylpyridin-3-yl)boronic acid → (S)-3-(3,6-dihydro-2H-pyran-4-yl)-7-(2-fluoro-4-methylpyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

HRID 335995Notes

Reaction equation

HRID 335995 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]=[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)=[C:27]([CH3:32])[CH:26]=[CH:25][N:24]=1.[O:33]1[CH2:38][CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH2:35][CH2:34]1>>[O:33]1[CH2:34][CH:35]=[C:36]([C:12]2[N:11]=[CH:10][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:28]2[C:23]([F:22])=[N:24][CH:25]=[CH:26][C:27]=2[CH3:32])=[CH:7][CH:6]=4)[CH2:37][CH2:38]1

Participants

4

Reactant 3

HCID 2763131(2-Fluoro-4-methylpyridin-3-yl)boronic acidHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 58466134(S)-7-bromo-3-chloro-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

Product 1

HCID 53464446(S)-3-(3,6-dihydro-2H-pyran-4-yl)-7-(2-fluoro-4-methylpyridin-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-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (prepared as described in Method BB41), 2-fluoro-4-methylpyridin-3-ylboronic acid and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Sources & evidence

ORD record
ord-4cc8b84ef84a42c1b74a605c8df4bb91
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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