Sodium hydride → 1-[(3-benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid

HRID 1901783Notes

Reaction equation

HRID 1901783 reaction equation
C([O:3][C:4](=[O:33])[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]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:19]=2)[C:7]=1[CH3:32])C.C(OC(=O)CC1C2C(=CC=C(OC)C=2)NC=1C)C.[H-].[Na+].C(OC1C=C(C=CC=1)CCl)C1C=CC=CC=1>>[CH2:25]([O:24][C:20]1[CH:19]=[C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[C:6]([CH2:5][C:4]([OH:33])=[O:3])=[C:7]2[CH3:32])[CH:23]=[CH:22][CH:21]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 105034151-[(3-Benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl esterHCID 10729163Ethyl (5-methoxy-2-methyl-1H-indol-3-yl)acetateHCID 131734903-(Benzyloxy)benzyl chloride

Product 1

HCID 233687631-[(3-benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acidYield 42%

Procedure

1-[(3-Benzyloxyphenyl)methyl]-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 465 mg (2 mmol) of meta-benzyloxybenzyl chloride and after chromatography on silica (eluting with 20% EtOAc/hexane) and crystallizing from MeOH there was obtained 376 mg (42%) of 1-[(3-benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid, mp, 60°-70° C.

Workup

  1. customafter chromatography on silica (eluting with 20% EtOAc/hexane) and crystallizing from MeOH

Sources & evidence

ORD record
ord-e09ae1c4789049a08a135cf93bc02c55
Source dataset
uspto-grants-1996_11
Patent number
US05578634

Reaction notes

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