Tripropylamine → 5-(2-Hydroxy-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966522Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:24])/[CH:10]=[C:11](/[NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][C:15]=1I)\[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CCC)CCC)CC>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][OH:22])[CH:18]=2)[NH:13][C:11]=1[CH3:12])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of (E)-3-[4-(2-hydroxy-ethyl)-2-iodo-phenylamino}-but-2-enoic acid benzyl ester (16.6 g, 38 mmol) and tripropylamine (7.2 mL, 38 mmol) in DMF (30 mL) was added palladium acetate (170 mg, 0.76 mmol). The mixture was stirred at 120° C. for 1 hour and then partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a residue, which was purified by chromatography (10%-30% ethyl acetate in hexanes) to give 3.0 g (26%) of the desired product as a white solid: mp 170-172° C.; MS(APCI+): m/z 310.4 (MH+); Anal. Calcd for C19H19N1O3.0.1H2O: C, 73.34; H, 6.22; N, 4.50. Found: C, 73.32; H, 6.37; N, 4.39.

Workup

custompartitioned between ethyl acetate and water
washThe organic phase was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customto give a residue, which
customwas purified by chromatography (10%-30% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-c26069b567be4a7888e4d968e7d50a2d
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951848B2

Reaction notes

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