Toluene → [4-(1-methyl-1H-imidazol-2-yl)-benzyl]-carbamic acid tert-butyl ester

HRID 911281Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].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>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:20]2[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

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

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

Sources & evidence

ORD record: ord-ac5f19b0b70d493981e888d300d960db
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022062B2

Reaction notes

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