Sodium hydride → HCID 53700123, compound

HRID 1069554

Reaction equation

HRID 1069554 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH3:26])=[CH:22][CH:23]=3)[C:18]([CH2:27][C:28]([OH:30])=[O:29])=[C:17]2[CH3:31])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:32](OC(=O)CC1C2C(=CC=C(OC)C=2)NC=1C)[CH3:33].[H-].[Na+].C(OC1C=CC(CCl)=CC=1)C1C=CC=CC=1>>[CH2:32]([O:29][C:28](=[O:30])[CH2:27][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[N:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[C:17]=1[CH3:31])[CH3:33]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 700424-Benzyloxybenzyl chlorideHCID 10729163Ethyl (5-methoxy-2-methyl-1H-indol-3-yl)acetateHCID 21191889HCID 21191889, compound

Product 1

HCID 53700123HCID 53700123, compound

Procedure

1-[(4-Benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid. Using the method described in Example 6, Part A, 2.0 g (8.12 mmol) of 5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester, 0.325 g (8.12 mmol) of 60% NaH/mineral oil, and 1.88 g (8.12 mmol) of 4-benzyloxy-1-chloromethylbenzene were reacted to give on workup 800 mg of crude 1-[(4-benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester. The crude ester in 50 mL of MeOH and 15 mL of 1N NaOH was heated at reflux temperature for 3 hours and left standing for 16 hours. After diluting with water, the mixture was made acidic with 1N HCl and extracted with EtOAc. The EtOAc solution was dried (Na2SO4) and concentrated. The residue was crystallized from MeOH to give 280 mg (32% yield) of 1-[(4-benzyloxyphenyl)-methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid, mp, 175-179° C.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-480e139e4306421181e72a34f0e7b9b8
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Linked notes

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