Ethyl 3-aminobenzoate → HCID 59463818, compound

HRID 1713400Notes

Reaction equation

HRID 1713400 reaction equation
CC([O-])(C)C.[K+].Br[C:8]1[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]([O:18][CH3:19])=[N:10][CH:9]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:29]=[CH:30][CH:31]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25].C(P(C1C=CC=CC=1C1C=CC=CC=1)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1>[CH3:19][O:18][C:11]1[C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=2[C:8]([NH:20][C:21]2[CH:22]=[C:23]([CH:29]=[CH:30][CH:31]=2)[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:9][N:10]=1

Participants

6

Reactant 4

HCID 11400Ethyl 3-aminobenzoateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23665647Potassium tert-butoxideHCID 59463819HCID 59463819, compound

Product 1

HCID 59463818HCID 59463818, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

580 mg (4.9 mmol) of 95% pure KOtBu are introduced into 20 ml of abs. toluene. After evacuation and ventilation with argon three times, 847 mg (3.5 mmol) of 4-bromo-1-methoxy-5,6,7,8-tetrahydroisoquinoline, and 868 mg (5.25 mmol) of ethyl 3-aminobenzoate are added. Addition of 160 mg (0.175 mmol) of tris(dibenzylidene)dipalladium and 209 mg (0.7 mmol) of di-tert-butylphosphinobiphenyl is followed by heating at 100° C. for three hours. For workup, the mixture is concentrated and the residue is partitioned between H2O and ethyl acetate. The phases are separated and the aqueous phase is extracted three times more. The combined organic phases are washed once more with H2O, dried with Na2SO4 and concentrated. Further purification takes place by chromatography on silica gel (CH2Cl2/MeOH 99:1), resulting in 640 mg of the title compound. Yield: 55%.

Workup

  1. concentrationFor workup, the mixture is concentrated
  2. customthe residue is partitioned between H2O and ethyl acetate
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted three times more
  5. washThe combined organic phases are washed once more with H2O
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customFurther purification

Sources & evidence

ORD record
ord-9599a8062c734d89b7d28304cf054591
Source dataset
uspto-grants-2010_09
Patent number
US07795278B2

Reaction notes

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