1-(Bromomethyl)-3-chlorobenzene → HCID 59253658, compound

HRID 1258154Notes

Reaction equation

HRID 1258154 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:13]=[N:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br.C(N(C(C)C)CC)(C)C>C(#N)C.ClCCl>[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8]2[N:13]=[N:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 81531DiisopropylethylamineHCID 59253661HCID 59253661, compound

Product 1

HCID 59253658HCID 59253658, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-(piperidin-4-ylamino)-pyridazine-3-carbonitrile (D3) (0.150 g, 0.74 mmol), 3-chlorobenzyl bromide (0.102 ml, 0.78 mol) and diisopropylethylamine (0.196 ml, 1.11 mol) in acetonitrile (2 ml) was stirred at 120° C. for 5 min., under microwave irradiation (Biotage MW-oven). The reaction mixture was then diluted with dichloromethane and extracted with a saturated solution of sodium carbonate. The organic layers were separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was then purified by column chromatography (silica gel; 0-2.5% ammonia in methanol (7 M)/dichloromethane). The desired fractions were collected and evaporated in vacuo, and the residue triturated with diisopropylether to yield E13 (0.095 g, 39%) as a white solid. C17H18ClN5 requires 327. Found 328 (MH+); mp: 151° C.

Workup

  1. extractionextracted with a saturated solution of sodium carbonate
  2. customThe organic layers were separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customThe residue was then purified by column chromatography (silica gel; 0-2.5% ammonia in methanol (7 M)/dichloromethane)
  7. customThe desired fractions were collected
  8. customevaporated in vacuo
  9. customthe residue triturated with diisopropylether

Sources & evidence

ORD record
ord-ff038c9b23b343b89baef3bfdb43f476
Source dataset
uspto-grants-2013_06
Patent number
US08466153B2

Reaction notes

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