(1-Bromoethyl)benzene → HCID 23368756, compound

HRID 1901784Notes

Reaction equation

HRID 1901784 reaction equation
C([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]([CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[C:7]=1[CH3:25])C.C(OC(=O)CC1C2C(=CC=C(OC)C=2)NC=1C)C.[H-].[Na+].BrC(C1C=CC=CC=1)C>>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:17]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:18])[C:7]([CH3:25])=[C:6]2[CH2:5][C:4]([OH:26])=[O:3]

Participants

5

Reactant 4

HCID 11454(1-Bromoethyl)benzeneHCID 24758Sodium hydrideHCID 10689282HCID 10689282, compoundHCID 10729163Ethyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate

Product 1

HCID 23368756HCID 23368756, compoundYield 22%

Procedure

5-Methoxy-2-methyl-1-(1-phenylethyl)-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 0.27 mL (2 mmol) of (1-bromoethyl)benzene and after chromatography on silica (eluting with 25% EtOAc/hexane) there was obtained 160 mg (22%) of 5-methoxy-2-methyl-1-(1-phenylethyl)1H-indole-3-acetic acid acid ethyl ester as an oil.

Sources & evidence

ORD record
ord-9c37a11f53fb4f88b92f8cf51efdc69a
Source dataset
uspto-grants-1996_11
Patent number
US05578634

Reaction notes

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