Water → HCID 90103171, compound

HRID 1051217Notes

Reaction equation

HRID 1051217 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]2[C:18]([O:24][CH3:25])=[N:19][CH:20]=[CH:21][C:22]=2[I:23])=[C:11]([N+:26]([O-])=O)[CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].O>P(OCC)(OCC)OCC>[C:1]([O:5][C:6](=[O:29])[N:7]([C:9]1[CH:10]=[C:11]2[C:12]([CH:15]=[C:16]([C:17]3[C:18]([O:24][CH3:25])=[N:19][CH:20]=[CH:21][C:22]=3[I:23])[NH:26]2)=[CH:13][CH:14]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 90102018HCID 90102018, compound

Product 1

HCID 90103171HCID 90103171, compoundYield 59%

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}-methyl-carbamic acid tert-butyl ester (1.00 g, 1.96 mmol) in triethyl phosphite (5.0 ml) was refluxed for 3 h. The reaction mixture was 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)-1H-indol-6-yl]-methyl-carbamic acid tert-butyl ester (550 mg, 59%) as a white solid. MH+ 479.7.

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-154b5b1b7eab4d7cb6c30186aecb081a
Source dataset
uspto-grants-2016_07
Patent number
US09388166B2

Reaction notes

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