Cesium carbonate → 1,1-Dimethylethyl [5-cyano-2-cyclopropyl-4-(trifluoromethyl)-1H-indol-1-yl]acetate

HRID 2102190Notes

Reaction equation

[CH:1]1([C:4]2[NH:5][C:6]3[C:11]([CH:12]=2)=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=3)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>C(#N)C>[C:17]([C:9]1[C:10]([C:13]([F:14])([F:15])[F:16])=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:4]([CH:1]1[CH2:2][CH2:3]1)=[CH:12]2)#[N:18]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 2-cyclopropyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 165A) (1.0 g, 4.0 mmol) in dry acetonitrile (25 mL) was added cesium carbonate (2.6 g, 8.0 mmol) and t-butyl bromoacetate (768 uL, 5.2 mmol) at rt. The mixture was stirred at 85° C. overnight. The solid was filtered and the filtrate was then concentrated in vacuo. The residue was triturated with EtOAc-hexane to afford the title compound (1.23 g) in quantitative yield: MS (ES) m/z 365 (M+1).

Workup

filtrationThe solid was filtered
concentrationthe filtrate was then concentrated in vacuo
customThe residue was triturated with EtOAc-hexane

Sources & evidence

ORD record: ord-d2fc2f445ea7453b970807ecfc814384
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572820B2

Reaction notes

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