m,alpha-Dichlorotoluene → HCID 10666953, compound

HRID 1901781Notes

Reaction equation

HRID 1901781 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2Cl)[C:7]=1[CH3:25])[CH3:2].C(OC(=O)CC1C2C(=CC=C(OC)C=2)NC=1C)C.[H-].[Na+].[Cl:47]C1C=C(C=CC=1)CCl>>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:47])[CH:19]=2)[C:7]=1[CH3:25])[CH3:2]

Participants

5

Reactant 4

HCID 12103m,alpha-DichlorotolueneHCID 24758Sodium hydrideHCID 10729163Ethyl (5-methoxy-2-methyl-1H-indol-3-yl)acetateHCID 10785480HCID 10785480, compound

Product 1

HCID 10666953HCID 10666953, compoundYield 55%

Procedure

1-(2-Chlorophenylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester. Using the procedure described in Example 1, Part F, 494 mg (2 mmol) of 5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester was reacted with 80 mg (2 mmol) of 60% NaH/mineral oil and 0.25 mL (2 mmol) of meta-chlorobenzylchloride and after chromatography on silica (eluting with 33% EtOAc/hexane) and crystallizing from MeOH there was obtained 409 mg (55%) of 1-(3-chlorophenylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester, mp, 79°-81° C.

Workup

  1. customafter chromatography on silica (eluting with 33% EtOAc/hexane) and crystallizing from MeOH

Sources & evidence

ORD record
ord-d55f00aa602c4198ad03a780f5609a53
Source dataset
uspto-grants-1996_11
Patent number
US05578634

Reaction notes

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