(5-Chloro-2-fluoropyridin-4-yl)boronic acid → (4-((5'-chloro-2'-fluoro-2,4'-bipyridin-6-ylamino)methyl)tetrahydro-2H-pyran-4-yl)methanol

HRID 1623425Notes

Reaction equation

HRID 1623425 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2([CH2:16][OH:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[C:20](B(O)O)=[CH:21][C:22]([F:25])=[N:23][CH:24]=1>>[Cl:18][C:19]1[C:20]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]([NH:8][CH2:9][C:10]3([CH2:16][OH:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[N:7]=2)=[CH:21][C:22]([F:25])=[N:23][CH:24]=1

Participants

3

Reactant 2

HCID 44754822(5-Chloro-2-fluoropyridin-4-yl)boronic acidHCID 86650645(4-((6-bromopyridin-2-ylamino)methyl)tetrahydro-2H-pyran-4-yl)methanol

Product 1

HCID 66937045(4-((5'-chloro-2'-fluoro-2,4'-bipyridin-6-ylamino)methyl)tetrahydro-2H-pyran-4-yl)methanol

Procedure

Following the same procedure as in Example 1b using (4-((6-bromopyridin-2-ylamino)methyl)tetrahydro-2H-pyran-4-yl)methanol (from step 3) and 5-chloro-2-fluoropyridin-4-ylboronic acid, the desired product was obtained. LCMS (m/z): 352 (MH+), retention time=0.54 min.

Sources & evidence

ORD record
ord-3a4b1407b02445619f2f86ca9211862a
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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