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Water → (R)-tert-Butyl 3-(4-(2-(cyclopropanecarboxamido)pyrazolo[1,5-a]pyridin-4-yl)phenoxy)pyrrolidine-1-carboxylate

HRID 873337
ノート
印刷プレビュー

反応式

HRID 873337 の反応式
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:25]2[CH:43]=[CH:42][C:28]([O:29][C@@H:30]3[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31]3)=[CH:27][CH:26]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1>[CH:14]1([C:12]([NH:11][C:9]2[CH:10]=[C:3]3[C:2]([C:25]4[CH:43]=[CH:42][C:28]([O:29][C@@H:30]5[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])[CH2:31]5)=[CH:27][CH:26]=4)=[CH:7][CH:6]=[CH:5][N:4]3[N:8]=2)=[O:13])[CH2:16][CH2:15]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 70979567N-(4-bromopyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamideHCID 86710535(R)-tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyrrolidine-1-carboxylate

生成物 1

HCID 86710536(R)-tert-Butyl 3-(4-(2-(cyclopropanecarboxamido)pyrazolo[1,5-a]pyridin-4-yl)phenoxy)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

N-(4-Bromopyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide (265 mg, 0.95 mmol), (R)-tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyrrolidine-1-carboxylate (442 mg, 1.14 mmol), PdCl2dppf (39 mg, 0.047 mmol) and Na2CO3 (501 mg, 4.73 mmol) were stirred in 1,4-dioxane (15 ml) and water (3 ml) and heated at 100° C. for 2 h. The reaction mixture was cooled to room temperature and filtered through celite. The residue was partitioned between EtOAc and water and the aqueous phase was extracted with EtOAc. The combined organics were dried (MgSO4), filtered and concentrated in vacuo to give (R)-tert-Butyl 3-(4-(2-(cyclopropanecarboxamido)pyrazolo[1,5-a]pyridin-4-yl)phenoxy)pyrrolidine-1-carboxylate as a brown oil which was used in the next step without further purification.

後処理

  1. filtrationfiltered through celite
  2. customThe residue was partitioned between EtOAc and water
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-df30dcaca0aa44a094237461751cc708
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08975406B2

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