Potassium Carbonate → HCID 58218641, compound

HRID 2063711Notes

Reaction equation

HRID 2063711 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[CH2:13][C:14]([O:16]CC)=[O:15])=[CH:4][CH:3]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:20][C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=1)[CH2:27][O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12099m-Xylyl bromideHCID 86652376HCID 86652376, compound

Product 1

HCID 58218641HCID 58218641, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(13A, 24.93 mg, 0.10 mmol) in DMF (1 mL) was added 1-(bromomethyl)-3-methylbenzene (19.6 mg, 0.105 mmol) following with K2CO3 (28 mg, 0.200 mmol). The reaction was stirred at 80° C. for 18 h. Volatile solvents were evaporated and the residue was diluted with 1:1 methanol:dioxane (0.35 0 mL, 0.152 M). To this solution was added 1M NaOH (0.350 mL) and the reaction was stirred at rt for 18 h. Volatile solvents were evaporated and the residue was diluted in DMF (1.250 mL) and distilled water (0.250 mL) and purified using Waters Sunfire (19×100 mm, 5 nm C18, 5:95 CH3CN:Water, 0.05% TFA) to yield Example 69. LC-MS Anal. Calc'd for C20H23NO3 325.40. found [M+H] 326.23.

Workup

  1. customVolatile solvents were evaporated
  2. additionthe residue was diluted with 1:1 methanol
  3. additionTo this solution was added 1M NaOH (0.350 mL)
  4. stirringthe reaction was stirred at rt for 18 h
  5. customVolatile solvents were evaporated
  6. additionthe residue was diluted in DMF (1.250 mL)
  7. distillationdistilled water (0.250 mL)
  8. custompurified
  9. customto yield Example 69

Sources & evidence

ORD record
ord-84d1c6d1286743cd822069919e1c0e93
Source dataset
uspto-grants-2012_10
Patent number
US08288404B2

Reaction notes

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