Bicyclo[2.2.1]hept-2-en-2-ylboronic acid → HCID 68312873, compound

HRID 1472909Notes

Reaction equation

HRID 1472909 reaction equation
C12CC(CC1)C=C2B(O)O.[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:26]2[CH2:27][N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][CH2:30][CH:31]=2)=[N:16][C:17]=1[CH2:18][NH:19][C@H:20]([CH:23]([CH3:25])[CH3:24])[CH2:21][OH:22]>[Pd]>[N:16]1[CH:17]=[CH:12][CH:13]=[CH:14][C:15]=1[C:26]1[CH2:27][N:28]([C:32]([O-:34])=[O:33])[CH2:29][CH2:30][CH:31]=1.[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH:26]2[CH2:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:27]2)=[N:16][C:17]=1[CH2:18][NH:19][C@H:20]([CH:23]([CH3:25])[CH3:24])[CH2:21][OH:22]

Participants

5

Reactant 2

HCID 44119810Bicyclo[2.2.1]hept-2-en-2-ylboronic acidHCID 68312512HCID 68312512, compound

Product 2

HCID 68312873HCID 68312873, compoundHCID 131732758HCID 131732758, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-tert-butyl 5-fluoro-6-4(1-hydroxy-3-methylbutan-2-yl)amino)methyl)-5′,6′-dihydro-[2,3′-bipyridine]-1′(2′H)-carboxylate was prepared according to Example 199, substituting tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for bicyclo[2.2.1]hept-2-en-2-ylboronic acid. (R)-tert-butyl 5-fluoro-6-(((1-hydroxy-3-methylbutan-2-yl)amino)methyl)-5′,6′-dihydro-[2,3′-bipyridine]-1′(2′H)-carboxylate was subjected to hydrogenation (H2 atmosphere, Pd/C catalyst) to provide the title compound. MS (ESI+) m/z 396 (M+H)+.

Sources & evidence

ORD record
ord-22f6137c6c0e47aebf9fa19d941b3435
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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