Hydrazine → 3-(4-isopropylpyrimidin-2-yl)-1H-indole-5-carbohydrazide
Reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([O:21]C)=O)[CH:17]=3)[N:12](S(C3C=CC(C)=CC=3)(=O)=O)[CH:11]=2)[N:5]=1)([CH3:3])[CH3:2].[NH2:33][NH2:34]>O1CCOCC1>[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([NH:33][NH2:34])=[O:21])[CH:17]=3)[NH:12][CH:11]=2)[N:5]=1)([CH3:2])[CH3:3]Participants
Conditions
- Temperature
- 90 °C
Procedure
A light-yellow mixture of methyl 3-(4-isopropylpyrimidin-2-yl)-1-tosyl-1H-indole-5-carboxylate (1.37 g, 3.05 mmol) in anhydrous hydrazine (2.39 mL, 76 mmol) and dioxane (1 mL) was heated in an oil bath at 90° C. for 3 h. The mixture was cooled to RT, treated with 20 mL of ice cold H2O. The precipitated pink solid was filtered, rinsed with 2×5 mL of water and 2×20 mL of EtOAc. The filtrate was transferred to a separatory funnel. The aqueous layer was discarded. The EtOAc layer was concentrated to half of its volume. The precipitated brown solid was filtered, rinsed with 2×2 mL of Et2O. The above obtained pink solid and brown solid were combined and dried in a vacuum oven at 40° C. for 18 h to afford 3-(4-isopropylpyrimidin-2-yl)-1H-indole-5-carbohydrazide (400 mg). This material was used in next step without further purification. MS (ESI, pos. ion) m/z: 296.1 (M+1).
Workup
- temperatureThe mixture was cooled to RT
- filtrationThe precipitated pink solid was filtered
- washrinsed with 2×5 mL of water and 2×20 mL of EtOAc
- customThe filtrate was transferred to a separatory funnel
- concentrationThe EtOAc layer was concentrated to half of its volume
- filtrationThe precipitated brown solid was filtered
- washrinsed with 2×2 mL of Et2O
- customThe above obtained pink solid and brown solid
- customdried in a vacuum oven at 40° C. for 18 h
Sources & evidence
- ORD record
- ord-4b6195e018874c3a8fee54ce8b2941fb
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321756B2
Reaction notes
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