Sodium Carbonate → 3-Cyano-4-hexyl-quinoline-6-carboxylic acid ethyl ester

HRID 1297680Notes

Reaction equation

HRID 1297680 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[N:17])=[C:9]2Cl)=[O:5])[CH3:2].[CH2:19](B(O)O)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[N:17])=[C:9]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 351064Hexylboronic Acid (contains varying amounts of Anhydride)HCID 585858234-Chloro-3-cyano-6-quinolinecarboxylic acid ethyl ester

Product 1

HCID 585858293-Cyano-4-hexyl-quinoline-6-carboxylic acid ethyl ester

Procedure

Similar procedure as described in example 46d was used, starting from 4-chloro-3-cyano-quinoline-6-carboxylic acid ethyl ester (example 46c), n-hexylboronic acid, sodium carbonate and POPd to give 3-cyano-4-hexyl-quinoline-6-carboxylic acid ethyl ester as a clear oil. LC-MS m/e 311 (MH+).

Sources & evidence

ORD record
ord-2718a961e2f940a58b7d0bf8bc502e09
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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