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

Sodium Carbonate → tert-butyl 4-(4-(4-(ethoxycarbonyl)-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)oxazol-5-yl)phenyl)piperazine-1-carboxylate

HRID 389738
ノート
印刷プレビュー

反応式

HRID 389738 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](I)[O:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)=[O:5])[CH3:2].CC1(C)C(C)(C)OB([C:39]2[CH:44]=[CH:43][N:42]=[C:41]3[NH:45][CH:46]=[CH:47][C:40]=23)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:39]2[CH:44]=[CH:43][N:42]=[C:41]3[NH:45][CH:46]=[CH:47][C:40]=23)[O:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 3

HCID 10340Sodium CarbonateHCID 497588714-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 68522092Tert-butyl 4-(4-(4-(ethoxycarbonyl)-2-iodooxazol-5-yl)phenyl)piperazine-1-carboxylate

生成物 1

HCID 59587460tert-butyl 4-(4-(4-(ethoxycarbonyl)-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)oxazol-5-yl)phenyl)piperazine-1-carboxylate収率 82%

試薬・触媒・溶媒 5

HCID 6102075
Dichlorobis(triphenylphosphine)palladium
触媒
HCID 702Ethanol溶媒
HCID 962Water溶媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of tert-butyl 4-(4-(4-(ethoxycarbonyl)-2-iodooxazol-5-yl)phenyl)piperazine-1-carboxylate (0.080 g, 0.15 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.093 g, 0.38 mmol) and sodium carbonate (0.048 g, 0.45 mmol) in toluene (0.81 ml), ethanol (0.49 ml) and water (0.23 ml) was added bis(triphenylphosphine)palladium (II) chloride (0.005 g, 0.007 mmol) and the resulting mixture irradiated in the microwave at 120° C. for 60 minutes. The reaction mixture was diluted with EtOAc and washed with H2O. The organic phase was passed through a MP-SH cartridge, dried over MgSO4 and the solvent removed in vacuo. The residue was purified by silica gel column chromatography using a 0-100% EtOAc in hexane gradient to afford tert-butyl 4-(4-(4-(ethoxycarbonyl)-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)oxazol-5-yl)phenyl)piperazine-1-carboxylate (0.070 g, 0.123 mmol, 81%) as a yellow solid. 1H NMR (CDCl3) δ 1.46 (3H, t), 1.49 (9H, s), 3.31 (4H, m), 3.61 (4H, m), 4.47 (2H, q), 7.00 (2H, d), 7.24 (1H, m), 7.55 (1H, m), 7.90 (1H, d), 8.18 (2H, d), 8.46 (1H, d), 10.68 (1H, br s). LCMS (3) Rt: 2.63 min; m/z (ES+) 518.

後処理

  1. customthe resulting mixture irradiated in the microwave at 120° C. for 60 minutes
  2. washwashed with H2O
  3. dry with materialdried over MgSO4
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-00260717e4724c25a8dacdabdffb074a
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08378095B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート