Water → HCID 58763622, compound

HRID 230269Notes

Reaction equation

HRID 230269 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.C([O-])(=O)C.[Na+].[Cl:17][C:18]1[CH:19]=[C:20]([CH3:41])[C:21]2[N:22]([C:24]([CH2:33][CH:34]([C:36]3[S:37][CH:38]=[CH:39][CH:40]=3)[OH:35])=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:26]=2)[CH:23]=1.O>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[C:20]([CH3:41])[C:21]2[N:22]([C:24]([CH2:33][C:34]([C:36]3[S:37][CH:38]=[CH:39][CH:40]=3)=[O:35])=[C:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:26]=2)[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium Acetate2×HCID 58763573HCID 58763573, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 58763622HCID 58763622, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dry round bottom flask was charged with anhydrous CH2Cl2 (2 mL), PCC (22 mg, 0.10 mmol) and sodium acetate/4 Å MS (1.1, 22 mg, 0.10 mmol NaOAc). To the suspension was added 2-(6-chloro-8-methyl-2-phenyl-imidazo[1,2-a]pyridin-3-yl)-1-thiophen-2-yl-ethanol 44d (19 mg, 0.05 mmol) dissolved in CH2Cl2 (1 mL). The resulting brown suspension was stirred at room temperature for 5 h. Water (5 mL) was added, and the crude reaction was washed with CH2Cl2 (3×20 mL). The organic washes were combined and washed with brine (1×20 mL), then dried (Na2SO4), filtered and concentrated. Purification by preparative TLC with 5% MeOH/CH2Cl2 gave the title compound (4.0 mg, 21%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.69 (s, 1H), 7.70-7.62 (m, 4H), 7.48-7.37 (m, 3H), 7.09 (at, 1H), 7.02 (s, 1H), 4.61 (s, 2H), 2.66 (s, 3H). Mass spectrum (m/e) 367 (M+1)+

Workup

  1. customthe crude reaction
  2. washwas washed with CH2Cl2 (3×20 mL)
  3. washwashed with brine (1×20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by preparative TLC with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-e14da80999794a6ea2d384dc99f33d23
Source dataset
uspto-grants-2009_07
Patent number
US07566725B2

Reaction notes

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