Potassium Carbonate → HCID 58449375, compound

HRID 2278752Notes

Reaction equation

HRID 2278752 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17](I)[CH:18]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)=[O:6].[NH:20]1[CH2:26][CH2:25][CH2:24][C@H:21]1[CH2:22][OH:23].C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>CS(C)=O.[Cu]I>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([N:20]2[CH2:26][CH2:25][CH2:24][C@H:21]2[CH2:22][OH:23])[CH:18]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)=[O:6]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 640091L-ProlinolHCID 58449366HCID 58449366, compound

Product 1

HCID 58449375HCID 58449375, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-bromo-5-iodo-N-((6-methylpyridin-3-yl)methyl)benzamide (250 mg, 0.58 mmol), L-prolinol (88 mg, 0.87 mmol), potassium carbonate (160 mg, 1.2 mmol), L-proline (13 mg, 0.12 mmol), and copper(I) iodide (11 mg, 0.058 mmol) in dimethyl sulfoxide (2 mL) under nitrogen was stirred at 90° C. for 10 h. The cooled mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column (EtOAc/hexane: 0-100%) to afford a white foam.

Workup

  1. customThe cooled mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column (EtOAc/hexane: 0-100%)
  8. customto afford a white foam

Sources & evidence

ORD record
ord-5629845579cd497fbb308233f126463c
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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