Potassium Carbonate → HCID 58020135, compound

HRID 1632086Notes

Reaction equation

HRID 1632086 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9]Br)[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[OH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][N:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]2=[O:13])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 58020164860584-79-8HCID 178516071HCID 178516071, compound

Product 1

HCID 58020135HCID 58020135, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Into a 100 mL round bottom flask was added 2-bromo-4-(2-bromo-ethyl)-1-methoxy-benzene (I-165, 1.82 g, crude), 2-hydroxypyridine (258 mg, 2.72 mmol), K2CO3 (625 mg, 4.53 mmol), and DME (20 mL). After stirring for 18 hours at 80° C. the suspension was filtered and the filtrate was concentrated. The residue was purified by flash column chromatography eluting with 25-50% acetone/hexanes to afford 221 mg of I-166 as a brown oil in 40% yield (2 steps).

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash column chromatography
  4. washeluting with 25-50% acetone/hexanes
  5. customto afford 221 mg of I-166 as a brown oil in 40% yield (2 steps)

Sources & evidence

ORD record
ord-fbce92b0c78d42c8b73f6cbf18468173
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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