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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
Notes
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Reaction equation

HRID 1465686 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 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-carboxylateYield 87.2%

Reagents, catalysts & solvents 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-9fb3fe16002e495aaad1cb4b734292ad
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08999966B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes