4-Fluorobenzoyl chloride → HCID 178505539, compound

HRID 2264200Notes

Reaction equation

[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[N:10][C:11]([NH2:15])=[C:12]([NH2:14])[CH:13]=1.[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=O)=[CH:25][CH:24]=1>N1C=CC=CC=1>[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]2[NH:15][C:11]3=[N:10][C:9]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)=[C:8]([C:7]4[CH:6]=[CH:5][N:4]=[CH:3][C:2]=4[F:1])[CH:13]=[C:12]3[N:14]=2)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 140 °C

Procedure

3″-Fluoro-3,2′:3′,4″-terpyridine-5′,6′-diamine (Intermediate 1,158 mg, 0.56 mmol), 4-fluorobenzoyl chloride (73.0 μL, 0.62 mmol) and pyridine (ca. 4 mL) were placed in a sealed tube. The solution was initially heated at 140° C. for 48 h and afterwards, at 160° C. for another 48 h. Then, the reaction mixture was cooled to room temperature, the pyridine was removed in vacuo, and the crude oil was purified by flash column chromatography (CH2Cl2/EtOH, 95:5) affording the title compound as a white solid (141 mg, 65%).

Workup

temperatureThen, the reaction mixture was cooled to room temperature
customthe pyridine was removed in vacuo
customthe crude oil was purified by flash column chromatography (CH2Cl2/EtOH, 95:5)

Sources & evidence

ORD record: ord-564af6489adb49eeacfaeb5d4c09c1d0
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855202B2

Reaction notes

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