Ammonium formate → methyl 2-(5-hydroxy-1H-indol-1-yl)propanoate

HRID 734390Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[CH:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15]CC3C=CC=CC=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:5].C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3](=[O:23])[CH:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(5-benzyloxy-indol-1-yl)-propionic acid methyl ester (Example 3, 20.0 g, 64.7 mmol) in absolute ethanol (150 mL) was added Pd(OH)2 (2.0 g, 10 wt %) suspended in ethanol (50 mL). Ammonium formate (8.1 g, 129.3 mmol) was added and the resulting mixture was heated to 60° C. for 4 h. The reaction mixture was cooled to rt and the palladium was filtered through a plug of silica gel. The filtrate was concentrated to give a light yellow oil which was used in the following step without further purification (13 g, 92%). LC/MS m/z 220 (M+H)+, RT 8.01 min; 1H NMR (400 MHz, acetone-d6) δ 7.78 (br s, 1H), 7.28 (d, 1H), 7.20 (d, 1H), 6.97 (d, 1H), 6.77 (dd, 1H), 6.36 (d, 1H), 5.23 (q, 1H), 3.62 (s, 3H), 1.78 (d, 3H).

Workup

temperatureThe reaction mixture was cooled to rt
filtrationthe palladium was filtered through a plug of silica gel
concentrationThe filtrate was concentrated
customto give a light yellow oil which
customwas used in the following step without further purification (13 g, 92%)
customLC/MS m/z 220 (M+H)+, RT 8.01 min

Sources & evidence

ORD record: ord-bf3fcce48b7242f891bdecc986464af6
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592361B2

Reaction notes

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