Triethylamine → HCID 19595279, compound

HRID 612447Notes

Reaction equation

HRID 612447 reaction equation
C(N(CC)CC)C.Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])=[CH:12][C:11]=1[CH2:27]Br.[NH:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[NH2:30]>CN(C)C=O.O.C(OCC)(=O)C>[CH3:19][CH:18]([Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[O:16][C:13]1[CH:12]=[C:11]2[C:10](=[CH:15][CH:14]=1)[CH2:9][N:30]([NH:29][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[CH2:27]2)[CH3:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 786452-HydrazinopyridineHCID 57072405HCID 57072405, compound

Product 1

HCID 19595279HCID 19595279, compoundYield 38.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (10.9 ml) was added to a solution of 1,2-dibromomethyl-4-[[tri(1-methylethyl)silyl]oxy]benzene (17 g) and 2-hydrazinopyridine (4.3 g) in dimethylformamide (300 ml), and the reaction mixture was stirred, under nitrogen, at ambient temperature for about 20 mins and then diluted with water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was triturated with ethyl acetate to yield 5.7 g (38%) of product. Recrystallization of the product from ethyl acetate gave the analytical sample mp 95-96° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-bd0c8b7df73c4a3381da1ebef8f20a02
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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