Water → HCID 90102936, compound

HRID 1051223Notes

Reaction equation

HRID 1051223 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[CH:13]=[C:12]([N+:14]([O-])=O)[C:11](/[CH:17]=[CH:18]/[C:19]2[C:20]([O:26][CH3:27])=[N:21][CH:22]=[CH:23][C:24]=2[I:25])=[CH:10][C:9]=1[O:28][CH3:29])([CH3:4])([CH3:3])[CH3:2].O>P(OCC)(OCC)OCC>[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[CH:13]=[C:12]2[C:11]([CH:17]=[C:18]([C:19]3[C:20]([O:26][CH3:27])=[N:21][CH:22]=[CH:23][C:24]=3[I:25])[NH:14]2)=[CH:10][C:9]=1[O:28][CH3:29])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 90102638HCID 90102638, compound

Product 1

HCID 90102936HCID 90102936, compoundYield 48%

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]-2-methoxy-5-nitro-phenyl}-carbamic acid tert-butyl ester (560 mg, 1.06 mmol) in triethyl phosphite (5.0 ml) was refluxed for 3 h, cooled to 25° C. and poured into water. 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)-5-methoxy-1H-indol-6-yl]-carbamic acid tert-butyl ester (250 mg, 48%) as a white solid. MH+ 496.0.

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-327c1021f1a34adc8f16332eb1bc752c
Source dataset
uspto-grants-2016_07
Patent number
US09388166B2

Reaction notes

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