Potassium Carbonate → 4-Methyl-3-(1-(3-oxopiperazin-1-yl)phthalazin-6-yl)benzamide

HRID 2357584ノート

反応式

HRID 2357584 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]1)=[N:7][N:6]=[CH:5]2.[CH3:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][C:21]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][C:21]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]1)=[N:7][N:6]=[CH:5]2

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 595448534-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 684552784-(6-Bromophthalazin-1-yl)piperazin-2-one

生成物 1

HCID 684523574-Methyl-3-(1-(3-oxopiperazin-1-yl)phthalazin-6-yl)benzamide収率 55.3%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 20074477Dimethoxyethane ethanol溶媒

反応条件

温度
90 °C

実験手順

A mixture of 4-(6-bromophthalazin-1-yl)piperazin-2-one (0.1 g, 0.3 mmol), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.09 g, 0.3 mmol), and tetrakis(triphenylphosphine)palladium (0.02 g, 0.02 mmol) in 5 mL DME/EtOH (4:1) was treated with 2M potassium carbonate (0.5 mL, 1.0 mmol). The mixture resulted was warmed up to 90° C. and stirred for 1 h under nitrogen. The mixture was cooled down to room temperature, and the crude product was purified via flash chromatography (silica gel) eluting with a gradient of 4% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM to give the title compound (60 mg) as a pale yellow solid. Found MS (ES+): 362(M+H)+.

後処理

  1. customThe mixture resulted
  2. temperatureThe mixture was cooled down to room temperature
  3. customthe crude product was purified via flash chromatography (silica gel)
  4. washeluting with a gradient of 4% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM

出典と根拠

ORDレコード
ord-23dcfc1281524dfc9abcfb8a0b603be7
出典データセット
uspto-grants-2010_07
特許番号
US07759337B2

反応ノート

読み込み中…