Diiodomethane → HCID 58827088, compound

HRID 76875Notes

Reaction equation

HRID 76875 reaction equation
[C:1](O)(C(F)(F)F)=O.[Zn](CC)CC.C(I)I.[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[CH:25]1[N:29]2[CH:30]=[N:31][CH:32]=[C:28]2[C:27](=[CH2:33])[CH2:26]1)[C:20]#[N:21]>C(Cl)Cl>[F:16][C:17]1[CH:18]=[C:19]([C:20]#[N:21])[CH:22]=[CH:23][C:24]=1[CH:25]1[N:29]2[CH:30]=[N:31][CH:32]=[C:28]2[C:27]2([CH2:1][CH2:33]2)[CH2:26]1

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 58827077HCID 58827077, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 58827088HCID 58827088, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of TFA (0.234 mL, 3 mmol) in 0.6 mL of dry CH2Cl2 is added dropwise to a solution of Et2Zn (1M in Hexanes, 3.06 mL, 3.06 mmol) at 0° C. The resulting suspension is subsequently treated with a solution of CH2I2 (0.246 mL, 3.06 mmol) in CH2Cl2 (0.4 mL). After 2 h at 0° C., a solution of 3-fluoro-4-(7-methylene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile (333.8 mg, 1.392 mmol) in CH2Cl2 is added. After overnight, the reaction is quenched with saturated NaHCO3 solution, and extracted with CH2Cl2 (20 mL×4). The combined extracts are washed with brine, dried over anhydrous Na2SO4. After filtration and evaporation, the residue is purified by chromatography and yield 112 mg of oil. MS (ESI) m/z 254.2 (M+H). 1H NMR (400.3 MHz, CDCl3): δ 8.93 (s, 1H), 7.54-7.52 (m, 1H), 7.45 (d, J=8.00 Hz, 1H), 7.35 (m, 1H), 6.83 (s, 1H), 6.27 (brs, 1H), 3.22 (m, 1H), 2.61 (d, J=12 Hz, 1H), 1.33-1.19 (m, 2H), 1.16-1.14 (m, 1H), 0.90-0.85 (m, 1H).

Workup

  1. waitAfter overnight
  2. customthe reaction is quenched with saturated NaHCO3 solution
  3. extractionextracted with CH2Cl2 (20 mL×4)
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration and evaporation
  7. customthe residue is purified by chromatography and yield 112 mg of oil

Sources & evidence

ORD record
ord-9fb0cb4fa8904cf9ab2751ce381a5954
Source dataset
uspto-grants-2014_09
Patent number
US08835646B2

Reaction notes

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