Potassium Carbonate → HCID 18455603, compound

HRID 1820644Notes

Reaction equation

HRID 1820644 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][C@H:12]1[O:17][C@@H:16]([CH3:18])[CH2:15][NH:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CC(OC)(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:14]2[CH2:13][CH:12]([CH3:11])[O:17][CH:16]([CH3:18])[CH2:15]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6415002,6-Dimethylmorpholine, cis-HCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 18455603HCID 18455603, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-bromo-2-fluorobenzaldehyde (16.0 g, 78.6 mmol), cis-2,6-dimethylmorpholine (9.32 g, 80.9 mmol), and potassium carbonate (15.0 g, 108 mmol) in DMF (75 mL) is heated in a 120° C. oil bath for 14 hours. The mixture is diluted with MTBE (250 mL) and washed with water (4×200 mL). (Ethyl acetate is added as needed to maintain the homogeneity of the organic layer). The organics are filtered through a 1″ plug of silica gel and evaporated to give 21.5 g of brown solid. This material is approximately 90% pure as judged by HPLC and is used without further purification. 1H NMR (DMSO-d6) δ 10.11, 7.78, 7.75, 7.17, 3.77-3.86, 3.12, 2.56, 1.11.

Workup

  1. washwashed with water (4×200 mL)
  2. addition(Ethyl acetate is added
  3. temperatureto maintain the homogeneity of the organic layer)
  4. filtrationThe organics are filtered through a 1″ plug of silica gel
  5. customevaporated

Sources & evidence

ORD record
ord-4ae55181870744a28b69b73d7b999b01
Source dataset
uspto-grants-2009_10
Patent number
US07605157B2

Reaction notes

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