Phenethyl bromide → HCID 118159836, compound

HRID 628253Notes

Reaction equation

HRID 628253 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[CH:12][NH:11][C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.CC#N>[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[CH:12][N:11]([CH:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH3:21])[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 136963115HCID 136963115, compound

Product 1

HCID 118159836HCID 118159836, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of 1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (10 mg, 0.058 mmol, isolated from Example 2, Step 5 during a preparation wherein the methylation of Step 2 of that Example was incomplete) and K2CO3 (0.024 g, 0.17 mmol) in DMF (0.22 mL) was added 1-(bromoethyl)benzene (12 μL, 0.087 mmol, Acros). The mixture was heated to 45° C. for 3 hours. The mixture was diluted with MeCN and filtered, then the product was isolated by preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (3.3 mg, 20%).

Workup

  1. customisolated from Example 2, Step 5 during a preparation wherein the methylation of Step 2 of that Example
  2. filtrationfiltered
  3. customthe product was isolated by preparative HPLC-MS (Waters XBridge C18
  4. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (3.3 mg, 20%)

Sources & evidence

ORD record
ord-5465aca40aaa418bbdbeb2ea3697b0a5
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

Loading…