Cesium carbonate → HCID 68941025, compound

HRID 2199763Notes

Reaction equation

HRID 2199763 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.Cl[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C[N-]C.CCOCC.O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 68938945ethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

Product 1

HCID 68941025HCID 68941025, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 182180DimethylazanideSolvent

Procedure

To a solution of ethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate (2.39 g, prepared in a similar manner as described herein) in N,N-dimethylamide (20 mL) was added 1-(chloromethyl)-4-methoxybenzene (1.0 g) and Cs2CO3 (5.16 g). The mixture was stirred overnight at room temperature. The mixture was diluted with ether (300 mL) and water (200 mL). The aqueous layer was extracted with ether. The combined extracts were washed with water (×3), brine and dried over Na2SO4. Concentration gave Example 581A.

Workup

  1. extractionThe aqueous layer was extracted with ether
  2. washThe combined extracts were washed with water (×3), brine
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration
  5. customgave Example 581A

Sources & evidence

ORD record
ord-0806ffa6c096455fa9a301bce93f206f
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

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