4,6-Dichloroindoline → 4-Chloro-5-fluoroindoline

HRID 544922Notes

Reaction equation

HRID 544922 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5](C(OCC)=O)[NH:6]2.ClC1C=C(Cl)C=C2C=1CCN2>>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2

Participants

3

Reactant 2

HCID 162444484,6-DichloroindolineHCID 18986263ethyl 4-chloro-5-fluoro-1H-indole-2-carboxylate

Product 1

HCID 441823394-Chloro-5-fluoroindoline

Procedure

The above ethyl 4-chloro-5-fluoroindole-2-carboxylate was treated in a manner similar to Reference Example 10-(3), (4) and 1 to give the titled compound, 4-chloro-5-fluoroindoline as a brown oil. APCI-Mass m/Z 172/174 (M+H). 1H-NMR (DMSO-d6) δ 2.97 (t, J=8.7 Hz, 2H), 3.48 (td, J=8.7, 1.9 Hz, 2H), 5.67 (s, 1H), 6.37 (dd, J=8.5, 3.7 Hz, 1H), 6.90 (t, J=9.2 Hz, 1H).

Sources & evidence

ORD record
ord-2b3a6d59dde54cb28a588000d983b020
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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