Hydrochloric Acid → 1-(1-(6-Chloropyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline

HRID 512821Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1.Cl.[Cl:18][C:19]1[N:20]=[N:21][C:22](Cl)=[CH:23][CH:24]=1.CCN(CC)CC>O.CS(C)=O>[Cl:18][C:19]1[N:20]=[N:21][C:22]([N:14]2[CH2:15][CH2:16][CH:11]([N:8]3[C:9]4[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=4)[CH2:6][CH2:7]3)[CH2:12][CH2:13]2)=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a 100 mL flask was placed 6-fluoro-1-(piperidin-4-yl)indoline as its corresponding HCl salt, prepared as in STEP 2 above (7.7 g, 30 mmol, 1 equiv) and 3,6-dichloropyridazine (4.69 g, 31.5 mmol, 1.05 equiv). DMSO (40 mL) and Et3N (12.54 mL, 90 mmol, 3 equiv) were added sequentially. The resulting mixture was heated at 80° C. for 7 h. The resulting mixture was then poured into vigorously stirred H2O (800 mL) and stirred for 1 h. The resulting solid was filtered and washed with H2O (30 mL×2), 50% Et2O/hexane (30 mL×2), and the dried to yield 1-(1-(6-chloropyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline as a solid.

Workup

customIn a 100 mL flask was placed
filtrationThe resulting solid was filtered
washwashed with H2O (30 mL×2), 50% Et2O/hexane (30 mL×2)
customthe dried

Sources & evidence

ORD record: ord-ccda1eb2a8cd4c5092009b0115eed6c6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102669B2

Reaction notes

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