5-Bromovaleric acid → HCID 86635534, compound

HRID 655100Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[C:10]2[C:9]3[CH:11]=[CH:12][C:13]([S:15]([O-:18])(=[O:17])=[O:16])=[CH:14][C:8]=3[CH:7]=[CH:6][C:5]=2[N:4]=[C:3]1[CH3:19].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28]>CC(C)C(=O)C>[C:27]([CH2:26][CH2:25][CH2:24][CH2:23][N+:4]1[C:5]2[CH:6]=[CH:7][C:8]3[CH:14]=[C:13]([S:15]([O-:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:9]=3[C:10]=2[C:2]([CH3:20])([CH3:1])[C:3]=1[CH3:19])([OH:29])=[O:28]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 1,1,2-trimethyl-1H-benzo[e]indole-7-sulfonic acid (723 mg, 2.5 mmol) in methanol (5 mL) was added a saturated solution of potassium hydroxide in isopropanol (3.134%, 4.913 g, 1.1 eq.) and the resulting suspension was heated at reflux for 2 h. Then the mixture was concentrated and the corresponding potassium salt was obtained. Under nitrogen atmosphere, a mixture of potassium 1,1,2-trimethyl-1H-benzo[e]indole-7-sulfonate and 5-bromovaleric acid (585 mg, 3 mmol) in 3-methyl-2-butanone (5 mL) was heated at 140° C. for 20 h. Removal of the solvent and purification by chromatography (dichloromethane/methanol) afforded 3-(4-carboxybutyl)-1,1,2-trimethyl-1H-benzo[e]indolium-7-sulfonate (70 mg, isolated yield 7.2%). LC-MS: 390.18 [M+].

Workup

customRemoval of the solvent and purification by chromatography (dichloromethane/methanol)

Sources & evidence

ORD record: ord-04578813cb134c4ea0b7bcdc111c57e0
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071388B2

Reaction notes

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