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Sodium Chloride → (R)-tert-butyl 3-(1-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl)piperidine-1-carboxylate

HRID 1465686
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HRID 1465686 반응식
[N:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[N:8]=[C:7]2[C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1)=[N+:2]=[N-:3].[C:38]([C@@H:40]1[CH2:45][CH2:44][CH2:43][N:42]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:41]1)#[CH:39].[Na+].[Cl-]>CC(O)(C)C.O>[N:35]1[CH:34]=[CH:33][C:32]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N:1]4[CH:39]=[C:38]([C@@H:40]5[CH2:45][CH2:44][CH2:43][N:42]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:41]5)[N:3]=[N:2]4)[CH:5]=3)[N:9]([C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:8]=2)=[CH:37][CH:36]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 5234Sodium ChlorideHCID 52420760tert-butyl (3S)-3-ethynylpiperidine-1-carboxylateHCID 866955715-azido-3-(pyridin-4-yl)-1-trityl-1H-indazole

생성물 1

HCID 67517916(R)-tert-butyl 3-(1-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl)piperidine-1-carboxylate수율 87.2%

시약·촉매·용매 1

HCID 71401949
2-Methylpropan-2-ol--water (1/1)
용매

실험 절차

5-azido-3-(pyridin-4-yl)-1-trityl-1H-indazole (1.0 g, 2.1 mmol) and (S)-tert-butyl 3-ethynylpiperidine-1-carboxylate (0.43 g, 2.1 mmol) were suspended in t-BuOH:H2O (1:1 10 mL:10 mL) and then CuSO4.5H2O (5 mg, 0.002 mmol) and Na-Ascorbic acid (40 mg, 0.21 mmol) were added sequentially. Reaction mixture was stirred vigorously at room temperature overnight. After the completion of reaction, added sat. NaCl (30 mL), extracted with EtOAc (3×50 mL), evaporated the organic solvent to give (R)-tert-butyl 3-(1-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl)piperidine-1-carboxylate (1.26 g) which was used for next step with out purification.

후처리

  1. customReaction mixture
  2. customAfter the completion of reaction
  3. extractionextracted with EtOAc (3×50 mL)
  4. customevaporated the organic solvent

출처 및 근거

ORD 기록
ord-9fb3fe16002e495aaad1cb4b734292ad
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08999966B2

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