Ethyl Acetate → HCID 86703971, compound

HRID 1773895Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]3[N:10]([CH2:11][CH2:12][C:13]4[CH:29]=[CH:28][CH:27]=[CH:26][C:14]=4[CH:15]3[O:18][CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[CH:9]=2)=[CH:4][CH:3]=1.[Cl:30]N1C(=O)CCC1=O.CCOC(C)=O.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:17]=[C:16]3[N:10]([CH2:11][CH2:12][C:13]4[CH:29]=[CH:28][CH:27]=[CH:26][C:14]=4[CH:15]3[O:18][CH:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)[C:9]=2[Cl:30])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(4-bromophenyl)-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 81A) (140 mg, 0.31 mmole) in CH2Cl2 (7 mL) cooled at 0° C. is added N-chlorosuccinimide (41 mg, 0.31 mmole). The reaction mixture is stirred at 0° C. for 1 h then is allowed to reach room temperature. Another portion of N-chlorosuccinimide (60 mg) is added. After 1 hour at room temperature, AcOEt is added and the reaction mixture is basified to pH 10 with 1N NaOH solution. The organic phase is washed with water, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH) with a gradient from (100:0) to (90:10) to give 2-(4-bromophenyl)-1-chloro-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene melting at 169° C.

Workup

customto reach room temperature
waitAfter 1 hour at room temperature
washThe organic phase is washed with water
dry with materialdried over magnesium sulphate
filtrationfiltered
customthe solvent is removed under reduced pressure
customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record: ord-87ba931692974d3a90b00e21668fdaa1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255101B2

Reaction notes

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