3,5-Dibromopyridine → HCID 86679134, compound

HRID 1774754Notes

Reaction equation

HRID 1774754 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]2([CH2:14][NH:13][CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20](Br)[CH:21]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]2([CH2:12][N:13]([C:20]3[CH:19]=[N:18][CH:17]=[C:16]([Br:15])[CH:21]=3)[CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 693693,5-DibromopyridineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 401519812-Boc-2,6-diazaspiro(3.3)heptane

Product 1

HCID 86679134HCID 86679134, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

In analogy to the procedure described for the preparation of intermediate A-3 [B], 2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester was reacted with 3,5-dibromopyridine in the presence of Pd2(dba)3, rac-BINAP and sodium tert-butoxide to give the title compound as a white solid.

Sources & evidence

ORD record
ord-bd2e8d6a798a49449e67ce06805cba19
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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