Cesium carbonate → Methyl 4-bromo-3-formyl-1-[3-(1-naphthalenyloxy)propyl]-1H-indole-2-carboxylate

HRID 1013302Notes

Reaction equation

HRID 1013302 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:15]=[O:16])=[C:5]([C:11]([O:13][CH3:14])=[O:12])[NH:6]2.Br[CH2:18][CH2:19][CH2:20][O:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:15]=[O:16])=[C:5]([C:11]([O:13][CH3:14])=[O:12])[N:6]2[CH2:18][CH2:19][CH2:20][O:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 129593811-(3-Bromopropoxy)naphthaleneHCID 71463951Methyl 4-bromo-3-formyl-1H-indole-2-carboxylate

Product 1

HCID 87353272Methyl 4-bromo-3-formyl-1-[3-(1-naphthalenyloxy)propyl]-1H-indole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 107A (1.76 g) in N,N-dimethylformamide (10 mL) was added 1-(3-bromopropoxy)naphthalene (1.66 g) and Cs2CO3 (6.10 g). The mixture was stirred for 3 days at room temperature. The mixture was diluted with ethyl acetate (300 mL) and water (200 mL). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water (×3) and brine and dried over Na2SO4. After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with water (×3) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration, concentration of solvent
  5. customgave crude product, which
  6. customwas purified by column chromatography (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9cb0f3e7c0c84ed399afdc792fdc2033
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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