Dichloromethane → HCID 59341976, compound

HRID 16010Notes

Reaction equation

HRID 16010 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.C(Cl)Cl.[CH2:25]([N:27](CC)CC)C>CC(N(C)C)=O.[C-]#N.[Zn+2].[C-]#N>[N:18]1[C:19]2[C:14](=[CH:13][C:12]([CH2:11][N:8]3[C:6]4=[N:7][C:2]([C:25]#[N:27])=[CH:3][N:4]=[C:5]4[N:10]=[N:9]3)=[CH:21][CH:20]=2)[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

Product 1

HCID 59341976HCID 59341976, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 6-[(6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl]quinoline (1.0 g, 2.93 mmol) in DMAC (70 ml) were added zinc cyanide (413 mg, 3.52 mmol). The reaction mixture was degassed then PdCl2(dppf).CH2Cl2 (240 mg, 0.29 mmol) was added followed with triethylamine (0.828 ml) at R.T. The reaction mixture was degassed again. After heating at 85° C., the reaction mixture was filtered through a celite pad and washed with 5.0 ml of CH2Cl2. The solvents were concentrated under reduced pressure. The resulting residue was purified via flash column chromatography eluted with 1-3% 7N N3 in MeOH:CH2Cl2 to give the desired product (740 mg, 88%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.28 (s, 2H) 7.55 (dd, J=8.34, 4.29 Hz, 1H) 7.81 (dd, J=8.72, 2.15 Hz, 1H) 7.99-8.04 (m, 2H) 8.33-8.37 (m, 1H) 8.91 (dd, J=4.04, 1.77 Hz, 1H) 9.41 (s, 1H) APCI (Mz+1) 288.2

Workup

  1. customThe reaction mixture was degassed
  2. customThe reaction mixture was degassed again
  3. filtrationthe reaction mixture was filtered through a celite pad
  4. washwashed with 5.0 ml of CH2Cl2
  5. concentrationThe solvents were concentrated under reduced pressure
  6. customThe resulting residue was purified via flash column chromatography
  7. washeluted with 1-3% 7N

Sources & evidence

ORD record
ord-205a032962f04956924f59a8bddc024b
Source dataset
uspto-grants-2010_06
Patent number
US07732604B2

Reaction notes

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