Bicyclo[2.2.1]hept-2-en-2-ylboronic acid → HCID 68312578, compound

HRID 1472911Notes

Reaction equation

HRID 1472911 reaction equation
C12CC(CC1)C=C2B(O)O.[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:26]2[CH2:27][CH2:28][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:30]=2)=[N:16][C:17]=1[CH2:18][NH:19][C@H:20]([CH:23]([CH3:25])[CH3:24])[CH2:21][OH:22]>[Pd]>[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:26]2[CH2:27][CH2:28][N:29]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH:30]=2)=[N:16][C:17]=1[CH2:18][NH:19][C@H:20]([CH:23]([CH3:25])[CH3:24])[CH2:21][OH:22].[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH:26]2[CH2:27][CH2:28][N:29]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:30]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 68312926HCID 68312926, compound

Product 2

HCID 68312578HCID 68312578, compoundHCID 68312926HCID 68312926, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-tert-butyl 4-(5-fluoro-6-(((1-hydroxy-3-methylbutan-2-yl)amino)methyl)pyridin-2-yl)-2,3-dihydro-1H-pyrrole-1-carboxylate was prepared according to Example 199, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-pyrrole-1-carboxylate for bicyclo[2.2.1]hept-2-en-2-ylboronic acid. (R)-tert-butyl 4-(5-fluoro-6-(((1-hydroxy-3-methylbutan-2-yl)amino)methyl)pyridin-2-yl)-2,3-dihydro-1H-pyrrole-1-carboxylate was subjected to hydrogenation (H2 atmosphere, Pd/C catalyst) to provide the title compound. MS (ESI+) m/z 2813 (M+H)+.

Sources & evidence

ORD record
ord-d75c4734651f41a6924aadde4bee5989
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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