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

Cesium carbonate → 7-[(2,5-dichloropyridin-4-yl)amino]-2-methyl-3H-isoindol-1-one

HRID 1045927
ノート
印刷プレビュー

反応式

HRID 1045927 の反応式
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[C:18](=[O:20])[N:17]([CH3:21])[CH2:16]2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[C:18](=[O:20])[N:17]([CH3:21])[CH2:16]3)[C:5]([Cl:9])=[CH:4][N:3]=1
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 10796Cesium carbonateHCID 450887127-Amino-2-methyl-2,3-dihydro-1H-isoindol-1-oneHCID 534009652,5-Dichloro-4-iodopyridine

生成物 1

HCID 866551387-[(2,5-dichloropyridin-4-yl)amino]-2-methyl-3H-isoindol-1-one収率 71.1%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒
HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2,5-dichloro-4-iodopyridine (0.2 g, 0.73 mmol), 7-amino-2-methyl-3H-isoindol-1-one (0.118 g, 0.73 mmol), palladium(II) acetate (6.56 mg, 0.03 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.025 g, 0.04 mmol) and cesium carbonate (0.476 g, 1.46 mmol) were suspended in dioxane (5 mL). The mixture was heated at 100° C. for 30 minutes in a microwave reactor and then allowed to cool to room temperature. The mixture was loaded onto an SCX column and the product eluted first with MeOH and then with a 7M solution of NH3 in MeOH. Fractions containing product were combined and evaporated. A solid recovered from the top of the column was washed with water, dried in vacuo, and combined with the evaporated residue to afford 7-[(2,5-dichloropyridin-4-yl)amino]-2-methyl-3H-isoindol-1-one (0.160 g, 71% yield); 1H NMR spectrum: (300 MHz, DMSO) δ 3.07 (3H, s), 4.50 (2H, s), 7.25-7.28 (1H, m), 7.48 (1H, s), 7.56-7.63 (2H, m), 8.36 (1H, s), 9.80 (1H, s); Mass spectrum: m/z (ESI+) (M+H)+=308.01 and 309.97 and 311.99.

後処理

  1. temperatureto cool to room temperature
  2. washthe product eluted first with MeOH
  3. additionFractions containing product
  4. customevaporated
  5. customA solid recovered from the top of the column
  6. washwas washed with water
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-19c0e7c2969548c7ae577ac0b5213d53
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08569298B2

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