Hydrazine, (2-chloro-4-fluorophenyl)- (9CI) → HCID 66664841, compound

HRID 1186823Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](F)[C:3]=1[CH:9]=O.[Cl:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[NH:19][NH2:20]>CN1C(=O)CCC1>[Cl:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[N:19]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([I:1])=[C:3]2[CH:9]=[N:20]1

Participants

Conditions

Temperature: 185 °C

Procedure

To a dry 15 mL ChemGlass pressure bottle under N2 was added 4-iodo-2-fluoro-3-formylpyridine (314 mg, 1.25 mmol), (2-chloro-4-fluorophenyl)hydrazine (210 mg, 1.31 mmol), and anhydrous NMP (5 mL). The reaction mixture was purged with argon, heated at 185° C. for 2 h, and then at 140° C. for 36 h. The reaction mixture was worked up according to the procedure described in Intermediate 69A and the crude product was purified by Biotage Silica gel chromatography using a 80 g Thompson Single Step™ silica cartridge with a linear gradient from 100% hexanes to 100% CH2Cl2 over 12 column volumes to give 63.5 mg (13.6%) of the title compound as a pale yellow solid, LC/MS (Condition B): ret. T=3.7 min, (M+H)+ 373.88, 375.88 and 149.3 mg (30.3%) of the hydrazone intermediate as a pale yellow solid, LC/MS (Condition B): ret. T=4.2 min, (M+H)+ 393.90, 395.90.

Workup

customThe reaction mixture was purged with argon
customthe crude product was purified by Biotage Silica gel chromatography

Sources & evidence

ORD record: ord-b8c3b22e698e4828b61e9e3823beb574
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673922B2

Reaction notes

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