Ethanol → HCID 59424800, compound

HRID 501062Notes

Reaction equation

[C:1]([O:5][C:6](=[O:17])[N:7]([C:9]1[C:14]([F:15])=[CH:13][C:12](Br)=[CH:11][N:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[O:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH:20]=[C:19]1B(O)O.CCN(CC)CC.C[CH2:38][OH:39]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:17])[N:7]([C:9]1[C:14]([F:15])=[CH:13][C:12]([C:19]2[O:18][C:22]3[CH:23]=[CH:24][C:25]([O:39][CH3:38])=[CH:26][C:21]=3[CH:20]=2)=[CH:11][N:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a degassed solution of (5-bromo-3-fluoro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester (310 mg, 1.01 mmol) in EtOH (10 mL) were added Pd(PPh3)2Cl2 (142 mg, 0.20 mmol), bezofuran boronic acid (291 mg, 1.52 mmol) and Et3N (283 μL, 2.03 mmol). The reaction was stirred in a microwave reactor for 30 minutes at 100° C. The volatiles were removed under reduced pressure and the residue was purified by flash column chromatography using 10% EtOAc in hexane to obtain title compound (130 mg) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.68 (br. s, 1 H) 7.80 (d, J=11.71 Hz, 1 H) 7.42 (d, J=8.98 Hz, 1 H) 7.04 (s, 2 H) 6.93 (dd, J=8.98, 2.34 Hz, 1 H) 3.85 (s, 3H) 3.35 (s, 3 H) 1.46 (s, 9 H). ESMS: m/z 359.41 (M+1)

Workup

customThe volatiles were removed under reduced pressure
customthe residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-c2f676beba9147ecb725ed8ce504e8e1
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772256B2

Reaction notes

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