Diiodomethane → HCID 178435273, compound

HRID 76255Notes

Reaction equation

HRID 76255 reaction equation
[CH3:1]OCCOC.C([Zn]CC)C.ICI.[CH:15](/[C:19]1=[CH:20][N:21]([C:36]([CH3:39])([CH3:38])[CH3:37])[S:22]/[C:23]/1=[N:24]\[C:25](=[O:35])[C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[O:33][CH3:34])=[CH:16]/[CH2:17][CH3:18]>C(Cl)Cl>[C:36]([N:21]1[CH:20]=[C:19]([CH:15]2[CH2:1][CH:16]2[CH2:17][CH3:18])/[C:23](=[N:24]/[C:25](=[O:35])[C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[O:33][CH3:34])/[S:22]1)([CH3:38])([CH3:37])[CH3:39]

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 80711,2-DimethoxyethaneHCID 178418750HCID 178418750, compoundHCID 178441285HCID 178441285, compound

Product 1

HCID 178435273HCID 178435273, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of CH2Cl2 (10 mL) and 1,2-dimethoxyethane (95 mg, 1.06 mmol) at −10° C. was added diethylzinc (130 mg, 1.06 mmol). To this solution was added dropwise diiodomethane (565 mg, 2.1 mmol). After the addition was complete, the resulting clear solution was stirred for 10 min at −10° C. A solution of Example 25B (200 mg, 0.53 mmol) was added to the reaction mixture, which was allowed to warm to room temperature and stir overnight. The reaction was quenched with NH4Cl then acetone and extracted with EtOAc (2×). The organics were combined, dried (MgSO4), filtered and solvent evaporated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 159 mg (77%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 0.59 (q, J=5.52 Hz, 1 H) 0.92 (t, J=7.36, 6.44 Hz, 3 H) 0.94-1.14 (m, 2 H) 1.16-1.29 (m, 2 H) 1.65 (s, 9 H) 2.11-2.33 (m, 1 H) 3.91 (s, 3 H) 6.91 (d, J=8.90 Hz, 1 H) 7.33 (dd, J=8.90, 2.76 Hz, 1 H) 7.81 (s, 1 H) 8.08 (d, J=2.76 Hz, 1 H); MS (DCI/NH4+) m/z 393 (M+H)+.

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. stirringstir overnight
  4. customThe reaction was quenched with NH4Cl
  5. extractionacetone and extracted with EtOAc (2×)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customsolvent evaporated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-aad092fb8f61483788075625ef18badd
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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