methyl 1H-indole-4-carboxylate → HCID 54402352, compound

HRID 1655056Notes

Reaction equation

HRID 1655056 reaction equation
C[Mg]Br.[NH:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[C:7]=2[CH:6]=[CH:5]1.[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[CH2:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1>C(OCCCC)CCC.CN(C)C=O>[CH3:16][O:15][C:13]([C:8]1[C:7]2[C:6]([CH2:33][C:32]3[CH:31]=[CH:30][C:29]([O:28][CH2:27][C:18]4[CH:19]=[CH:20][C:21]5[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=5)[N:17]=4)=[CH:36][CH:35]=3)=[CH:5][NH:4][C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:14]

Participants

6

Reactant 3

HCID 2733668methyl 1H-indole-4-carboxylateHCID 147741632-(4-Chloromethylphenoxy)methylquinolineHCID 178418573HCID 178418573, compound

Product 1

HCID 54402352HCID 54402352, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8909Butyl etherSolvent

Procedure

A solution of methyl magnesium bromide in n-butyl ether (1.0M, 10.3 ml) was added dropwise to a solution of methyl indole-4-carboxylate (1.5 g) in dry dimethylformamide (15 ml) stirred under an atmosphere of nitrogen at room temperature. The mixture was stirred at room temperature for 20 minutes then a solution of 4-(quinolin-2-ylmethoxy)benzyl chloride (Example 1a) (2.35 g) in dry dimethylformamide (10 ml) added dropwise. The mixture was stirred at room temperature overnight, concentrated in vacuo, diluted with ethyl acetate and washed with water and a saturated solution of ammonium chloride; the organic phase was dried, filtered and evaporated. The residue was purified by chromatography on flash silica, eluting with petroleum spirit 40°-60° C.--diethyl ether (1:1) to give the product as a white solid. A small quantity was crystallised from petroleum spirit 40°-60° C.--diethyl ether (1:1), m.p. 148°-150° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 20 minutes
  2. stirringThe mixture was stirred at room temperature overnight
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. customthe organic phase was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by chromatography on flash silica
  10. washeluting with petroleum spirit 40°-60° C.

Sources & evidence

ORD record
ord-f3847ded8c884b36895affb2a38109c1
Source dataset
uspto-grants-1995_04
Patent number
US05410061

Reaction notes

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