Sodium Hydroxide → HCID 9823988, compound

HRID 1975984Notes

Reaction equation

HRID 1975984 reaction equation
N[C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[CH:8]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:5]2=[N:6][CH:7]=1.[Br:28]Br.N([O-])=O.[Na+].[OH-].[Na+]>Br.O>[Br:28][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[CH:8]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 20651504HCID 20651504, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 9823988HCID 9823988, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 4-(3-amino-6,11-dihydro-5H-cyclohepta[2,1-b:4,5-b′]dipyridin-11-yl)-1-piperidinecarboxylate ( 0.05 gm, 0.136 mmol) was dissolved in 4 ml of 48% hydrobromic acid. The reaction mixture was cooled to 0° C. and bromine (0.038 ml, 0.738 mmol) was added dropwise and stirred for 15 minutes. Sodium nitrite (0.028 gm, 0.408 mmol) was added, as a solution in 0.5 ml of water, dropwise over 15 minutes. The reaction was stirred at 0° C. for 3-4 hours. The reaction mixture was basified to pH 10 with 10% sodium hydroxide and the produt extracted into ethylacetate. The ethylacetate layer was dried over magnesium sulfate, filtered and evaporated to dryness. The crude product was chromatographed on silica gel using 10-20% methanol/dichoromethane as the eluent to obtain 0.035 gm of title product. FABMS (M+1)=431

Workup

  1. stirringThe reaction was stirred at 0° C. for 3-4 hours
  2. extractionthe produt extracted into ethylacetate
  3. dry with materialThe ethylacetate layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was chromatographed on silica gel using 10-20% methanol/dichoromethane as the eluent

Sources & evidence

ORD record
ord-7160101d69bd4bf4a79dee74f7d42d7e
Source dataset
uspto-grants-2001_05
Patent number
US06225322B1

Reaction notes

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