Toluene → (4-(1-Methyl-1H-imidazol-2-yl)phenyl)methanamine

HRID 2041170Notes

Reaction equation

HRID 2041170 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1)=O)(C)(C)C.Br[C:20]1[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>CCOC(C)=O.[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>[CH3:25][N:21]1[CH:22]=[CH:23][N:24]=[C:20]1[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH2:8])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27732622-Bromo-1-methyl-1H-imidazoleHCID 38631634-(tert-Butoxycarbonylaminomethyl)phenylboronic acid

Product 1

HCID 57656174(4-(1-Methyl-1H-imidazol-2-yl)phenyl)methanamineYield 128.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

[4-(1-Methyl-1H-imidazol-2-yl-benzyl]-carbamic acid tert-butyl ester: Add 4-(N-tert-Butoxycarbonyl-aminomethyl)phenylboronic acid (1.9 g, 7.4 mmol), 2-bromo-1-methyl-1H-imidazole (800 mg, 5.0 mmol), tetrakis(triphenylphosphine)-palladium(0) (287 mg, 0.25 mmol) and potassium carbonate (860 mg, 6.2 mmol) to a flask containing toluene (10 mL). Heat the mixture in a sealed flask at 90° C. for 16 h. Cool the mixture, dilute with EtOAc (50 mL), filter through Celite®, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc/methanol (49:50:1) to obtain the desired intermediate (1.2 g, 83%). GC-MS m/z: 287 (M+).

Workup

  1. temperatureCool the mixture
  2. filtrationfilter through Celite®
  3. concentrationconcentrate in vacuo
  4. customPurify by chromatography on silica gel eluting with hexane/EtOAc/methanol (49:50:1)

Sources & evidence

ORD record
ord-302509d333144d35affded7f288d5cd4
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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