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

HRID 533260Notes

Reaction equation

HRID 533260 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-6ea4b6766b1a41c3808bfedde8ae15e8
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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