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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
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HRID 873337 반응식
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
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-df30dcaca0aa44a094237461751cc708
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975406B2

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