Water → HCID 90102638, compound

HRID 1051222Notes

Reaction equation

HRID 1051222 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH2:17][CH:18](OC(=O)C(F)(F)F)[C:19]2[C:20]([O:26][CH3:27])=[N:21][CH:22]=[CH:23][C:24]=2[I:25])=[C:11]([N+:35]([O-:37])=[O:36])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:10]=[C:11]([N+:35]([O-:37])=[O:36])[C:12](/[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:13][C:14]=1[O:15][CH3:16])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 90102232HCID 90102232, compound

Product 1

HCID 90102638HCID 90102638, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of crude trifluoro-acetic acid 2-(4-tert-butoxycarbonylamino-5-methoxy-2-nitro-phenyl)-1-(4-iodo-2-methoxy-pyridin-3-yl)-ethyl ester (crude 1.35 g, 2.12 mmol) in THF (10 mL) was added 8-diazabicyclo[5.4.0]undec-7-ene (1.48 g, 9.75 mmol) at 25° C. The reaction was allowed to stir at 70° C. 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 (80/20 hexanes/ethyl acetate) afforded {4-[(E)-2-(4-iodo-2-methoxy-pyridin-3-yl)-vinyl]-2-methoxy-5-nitro-phenyl}-carbamic acid tert-butyl ester (560 mg, 55%) as an oil. MH+ 527.8.

Workup

  1. temperaturecooled to 25° C.
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. concentrationfollowed by concentration in vacuo
  7. customgave a brown solid

Sources & evidence

ORD record
ord-d6b8c095720d4fb18c76d53165af348d
Source dataset
uspto-grants-2016_07
Patent number
US09388166B2

Reaction notes

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