Water → HCID 74220601, compound

HRID 1051211Notes

Reaction equation

HRID 1051211 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]2[C:17]([O:23][CH3:24])=[N:18][CH:19]=[CH:20][C:21]=2[I:22])=[C:10]([N+:25]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O>P(OCC)(OCC)OCC>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:9]=[C:10]2[C:11]([CH:14]=[C:15]([C:16]3[C:17]([O:23][CH3:24])=[N:18][CH:19]=[CH:20][C:21]=3[I:22])[NH:25]2)=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 90102988HCID 90102988, compound

Product 1

HCID 74220601HCID 74220601, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 31215Triethyl phosphiteSolvent

Conditions

Temperature
25 °C

Procedure

A solution of {4-[(E)-2-(4-iodo-2-methoxy-pyridin-3-yl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester (800 mg, 1.61 mmol) in triethyl phosphite (16.0 ml) was refluxed for 3 h. The reaction mixture was cooled to 25° C. and poured into water and the aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (70/30 hexanes/ethyl acetate) afforded [2-(4-iodo-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-carbamic acid tert-butyl ester (250 mg, 33%) as a white solid. MH+ 465.9.

Workup

  1. extractionthe aqueous phase was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration
  5. concentrationfollowed by concentration in vacuo
  6. customgave a brown solid

Sources & evidence

ORD record
ord-ae96935660ef4d5789107146cdec628c
Source dataset
uspto-grants-2016_07
Patent number
US09388166B2

Reaction notes

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