Cesium carbonate → HCID 58230554, compound

HRID 390402Notes

Reaction equation

HRID 390402 reaction equation
[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4]2([CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[CH2:3]1.Br[CH2:17][C:18]1[CH:41]=[CH:40][C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C@@H:30]([C:37]#[C:38][CH3:39])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4]2([CH2:5][CH2:6][N:7]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:22][O:23][C:24]4[CH:29]=[CH:28][C:27]([C@@H:30]([C:37]#[C:38][CH3:39])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:26][CH:25]=4)=[CH:40][CH:41]=3)[CH2:8][CH2:9]2)[CH2:3]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 106557391-Methyl-1,2-dihydrospiro[indole-3,4'-piperidine]HCID 58230603HCID 58230603, compound

Product 1

HCID 58230554HCID 58230554, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-methylspiro[indoline-3,4′-piperidine] (0.0486 g, 0.204 mmol), ethyl (3S)-3-(4-{[4-(bromomethyl)benzyl]oxy}phenyl)hex-4-ynoate (0.100 g, 0.24 mmol), and Cs2CO3 (0.156 g, 0.48 mmol) in DMF (5 mL) is stirred at room temperature for 16 hours. The reaction mixture is diluted with water (30 mL) and extracted with EtOAc (3×25 mL). The combined organic layer is washed with water (3×25 mL) and saturated brine solution (25 mL), dried with a drying agent, filtered, and evaporated to dryness to give a liquid. The crude product is purified by silica gel chromatography (gradient EtOAc/hexane 30%) to give the title compound as a colourless liquid (0.095 g, 73.3%). ESI/MS m/z 537 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe combined organic layer is washed with water (3×25 mL) and saturated brine solution (25 mL)
  3. customdried with a drying agent
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto give a liquid
  7. customThe crude product is purified by silica gel chromatography (gradient EtOAc/hexane 30%)

Sources & evidence

ORD record
ord-0ab6dc1764dc4ee5913be224bbf8b9c5
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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