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

HRID 966522
Notes
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Reaction equation

HRID 966522 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7616TripropylamineHCID 23393857(E)-3-[4-(2-Hydroxy-ethyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl Ester

Product 1

HCID 233938725-(2-Hydroxy-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl EsterYield 26%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228
Dimethylformamide
Solvent

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

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a residue, which
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes