ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Potassium Carbonate → 5-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester

HRID 1025570
ノート
印刷プレビュー

反応式

HRID 1025570 の反応式
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[CH:26]=[CH:25][CH:24]=[C:23](B3OC(C)(C)C(C)(C)O3)[C:17]=1[CH2:18][O:19][C:20](=[O:22])[CH3:21])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[CH3:36][O:37][C:38]([C:40]1[N:41]([CH3:46])[C:42](Br)=[CH:43][CH:44]=1)=[O:39].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:36][O:37][C:38]([C:40]1[N:41]([CH3:46])[C:42]([C:23]2[CH:24]=[CH:25][CH:26]=[C:16]([N:10]3[N:9]=[CH:8][C:7]4[C:12](=[CH:13][CH:14]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[CH:6]=4)[C:11]3=[O:15])[C:17]=2[CH2:18][O:19][C:20](=[O:22])[CH3:21])=[CH:43][CH:44]=1)=[O:39]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 22350505Methyl 5-bromo-1-methyl-1H-pyrrole-2-carboxylateHCID 580162042-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate2 回

生成物 1

HCID 710081245-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester収率 77%

試薬・触媒・溶媒 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

Under N2, a mixture of acetic acid 2-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl ester (described in the preparation of intermediate 4, 300 mg, 0.63 mmol), 5-bromo-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (150 mg, 0.69 mmol), Pd(dppf)Cl2 (150 mg, 0.19 mmol) and K2CO3 (261 mg, 1.9 mmol) in dioxane (15 mL) and water (3 mL) were heated at 100° C. for 3 h. The mixture was concentrated to dryness. The residue was purified by silica gel column chromatography (eluted with petroleum ether/ethyl acetate from the ratio of 8:1 to 5:1) to give 5-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (237 mg, yield 77%) as a yellow liquid. LC-MS calcd for C28H29N3O5 (m/e) 487.21, obsd 997 [2M+Na]+.

後処理

  1. concentrationThe mixture was concentrated to dryness
  2. customThe residue was purified by silica gel column chromatography (
  3. washeluted with petroleum ether/ethyl acetate from the ratio of 8:1 to 5:1)

出典と根拠

ORDレコード
ord-25d3592834484df2ae16c32ee9f01188
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08729078B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート