3-(2-Chloro-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole → 3-(2-Cyclopropyl-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole
Reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.Cl[C:7]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=3)[N:15]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:14]=2)[CH:10]=[CH:9][N:8]=1>[Cl-].[Cl-].[Zn+2].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.CN1C(=O)CCC1>[CH:1]1([C:9]2[CH:10]=[C:11]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=4)[N:15]([C:25]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:14]=3)[CH:12]=[CH:7][N:8]=2)[CH2:3][CH2:2]1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To a tube under nitrogen was added 36.2 ml ZnCl2 (0.5 M in THF, 18.02 mmol) followed by cyclopropylmagnesium bromide (34 ml of 0.5 M in THF soln., 16 mmol). The resultant mixture was stirred for 20 min at r.t. NMP (23 ml) was added, stirred for 5 min followed by 3-(2-Chloro-pyridin-4-yl)-5-nitro-1-trityl-1H-indazole (5.5 gm, 10.6 mmol) and Pd[P(tBu)3]2 (0.108 gm, 0.22 mmol). The tube was sealed under nitrogen and stirred at 100 C for 18 hrs. The reaction mixture was then cooled and evaporated to dryness. Silica gel chromatography using 5-20% ethylacetate/hexanes gave 2.1 g of title product.
Workup
- customThe tube was sealed under nitrogen
- stirringstirred at 100 C for 18 hrs
- temperatureThe reaction mixture was then cooled
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-a03579c846464ff894901abb7c06dcbf
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546404B2
Reaction notes
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