Phenylboronic Acid → HCID 9930531, compound

HRID 1077564Notes

Reaction equation

HRID 1077564 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[C:14]=1[CH2:15][O:16][CH3:17])=[CH:11][C:10]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:9][CH:8]=3.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:19]([O:18][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5]1[CH:4]=[N:3][C:2]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:14]([CH2:15][O:16][CH3:17])[C:13]2=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 66827Phenylboronic AcidHCID 19431936HCID 19431936, compound

Product 1

HCID 9930531HCID 9930531, compoundYield 78.7%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

476 mg of 3-bromo-6-benzyloxy-4-methoxymethyl-β-carboline is introduced in 10 ml of toluene and 5 ml of ethanol, mixed with 41 mg of tetrakis(triphenylphosphine)-palladium(0) and stirred for 5 minutes. Then 177 mg of phenylboronic acid and 1.5 ml of a 2 m- soda solution are added and then heated for 3 hours to 95° C. After concentration by evaporation it is taken up in a lot of ethyl acetate and washed once each with water and saturated common salt solution. After drying, filtration and concentration by evaporation, it is recrystallized. 372 mg of 6-benzyloxy-3-phenyl-4-methoxymethyl-β-carboline of a melting point of 205°-206° C. (ethanol, methylene chloride, hexane) is obtained.

Workup

  1. temperatureheated for 3 hours to 95° C
  2. concentrationAfter concentration
  3. customby evaporation it
  4. washwashed once each with water and saturated common salt solution
  5. customAfter drying
  6. filtrationfiltration and concentration
  7. customby evaporation, it
  8. customis recrystallized

Sources & evidence

ORD record
ord-76039ac1fd37463ebbf0afbb73059145
Source dataset
uspto-grants-1996_08
Patent number
US05543519

Reaction notes

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