Water → HCID 86623344, compound

HRID 1986348Notes

Reaction equation

HRID 1986348 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:19][C:20]([Si:23]([CH3:33])([CH3:32])[O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)([CH3:22])[CH3:21].O>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:29][C:28]2[CH:27]=[CH:26][C:25]([O:24][Si:23]([C:20]([CH3:22])([CH3:21])[CH3:19])([CH3:32])[CH3:33])=[CH:31][CH:30]=2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 117155534-((Tert-butyldimethylsilyl)oxy)anilineHCID 122757652,4-Dichloro-5-nitropyridine

Product 1

HCID 86623344HCID 86623344, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Example 1, Step 3 (20.0 g, 104 mmol) and triethylamine (17.4 mL, 125 mmol) were dissolved in THF (200 mL) and a solution of 4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}aniline (25.0 g, 113 mmol) in THF (50 mL) was added and the mixture was allowed to stir at rt overnight. The reaction mixture was poured into water and extracted with EtOAc. The combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated to give the title compound (37.5 g, 95%) as a yellow oil. MS (ES+) m/e 381 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ba26645cdfd74dd4a83fc210d02e8c36
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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