3-Amino-2-bromopyridine → HCID 10131088, compound

HRID 1835855Notes

Reaction equation

HRID 1835855 reaction equation
Br[C:2]1[C:7]([NH:8][C:9]([C:11]2[CH2:12][N:13]([C:17](OC(C)(C)C)=O)[CH2:14][CH2:15][CH:16]=2)=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[C:25]1[C:30](N)=CC=CN=1.COC(C1CN(C(OC(C)(C)C)=O)CCC=1)=O.C[Al](C)C>C(Cl)Cl>[CH2:17]([N:13]1[CH2:14][CH2:15][CH2:16][C:11]2([C:2]3[C:7](=[CH:6][CH:5]=[CH:4][N:3]=3)[NH:8][C:9]2=[O:10])[CH2:12]1)[CH2:25][CH3:30]

Participants

6

Reactant 4

HCID 6428163-Amino-2-bromopyridineHCID 111284441-Tert-butyl 3-methyl 1,2,5,6-tetrahydropyridine-1,3-dicarboxylateHCID 16682925TrimethylaluminumHCID 23500685HCID 23500685, compound

Product 1

HCID 10131088HCID 10131088, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-[(2-bromo-3-pyridyl)carbamoyl]-1,2,5,6-tetrahydropyridine-1-carboxylate. 2-Bromo-3-pyridineamine (3.0 g, 17.3 mmol) and 1,2,5,6-tetrahydro-1,3-pyridinedicarboxylic acid 1-tert-butyl ester 3-methyl ester (5.05 g, 20.8 mmol) were dissolved in DCM (80 ml). To the solution trimethylaluminium (26 mmol, 2M solution) was slowly added at 0° C. The mixture was refluxed overnight. Work-up and purification on silica gel using 60% ethyl acetate in heptane as an eluent gave 5.65 g (85%) of the title compound.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. custompurification on silica gel using 60% ethyl acetate in heptane as an eluent

Sources & evidence

ORD record
ord-982646ad44094d54ba4efa11887409ba
Source dataset
uspto-grants-2004_08
Patent number
US06774132B1

Reaction notes

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