HCID 23365902, compound → Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

HRID 1904475Notes

Reaction equation

HRID 1904475 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11]C)[CH:6]=[C:5]2[CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[O:24][CH3:25]>O1CCCC1.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[O:24][CH3:25]

Participants

4

Reactant 1

HCID 23365902HCID 23365902, compound

Product 1

HCID 11209537Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (F') (0.56 g) in tetrahydrofuran (30 ml) was hydrogenated in the presence of palladium-on-carbon (10% w/w; 0.1 g), as described for the amino ester (H) in Example 4, to give methyl 4-(5-amino-1-methylindol-3-ylmethyl)-3-methoxybenzoate (S) (0.50 g, 98%) as pale yellow foam; NMR: 3.6(s, 3H, NCH3), 3.8(s, 3H, COOCH3), 3.9(br s, 5H, OCH3 and CH2Ar), 4.45(br, 2H, NH2), 6.54(m, 2H), 6.86(s, 1H), 7.04(m, 2H), 7.40(m, 2H).

Sources & evidence

ORD record
ord-cfc3ff905e3a450fa48348d0c936cf85
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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