Water → 1-Cyclopropyl-2-[4-(isopropylamino)phenyl]-6-pyrimidin-2-yloxy-indole-3-carbonitrile

HRID 506136Notes

Reaction equation

[CH:1]1([N:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=3)[C:6]([C:14]#[N:15])=[C:5]2[C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:33]1[N:38]=[CH:37][CH:36]=[CH:35][N:34]=1.O>CN(C=O)C>[CH:1]1([N:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:33]4[N:38]=[CH:37][CH:36]=[CH:35][N:34]=4)[CH:11]=3)[C:6]([C:14]#[N:15])=[C:5]2[C:16]2[CH:17]=[CH:18][C:19]([NH:22][CH:23]([CH3:25])[CH3:24])=[CH:20][CH:21]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of (1-cyclopropyl-6-hydroxy-2-(4-isopropylamino-phenyl)-1H-indole-3-carbonitrile (0.099 g, 0.3 mmol), Cs2CO3 (0.244 g, 0.75 mmol), 2-chloropyrimidine (0.069 g, 0.6 mmol) in DMF (2.0 mL) was stirred at 70° C. overnight. After cooling to room temperature the mixture was poured into water (15 mL) and the precipitate was collected via filtration and washed with water and purified on silica gel (CH2Cl2/EtOAc, 9:1) to provide 1-cyclopropyl-2-(4-isopropylamino-phenyl)-6-(pyrimidin-2-yloxy)-1H-indole-3-carbonitrile as a solid (0.104 g, 85%).

Workup

temperatureAfter cooling to room temperature the mixture
filtrationthe precipitate was collected via filtration
washwashed with water
custompurified on silica gel (CH2Cl2/EtOAc, 9:1)

Sources & evidence

ORD record: ord-0d0cc7093d68405eb3ca20ad459a473f
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781478B2

Reaction notes

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