Dimethyl Sulfoxide → HCID 22638715, compound

HRID 1836654Notes

Reaction equation

HRID 1836654 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH:13]1[CH2:15][CH:14]1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]#[N:26])[CH:23]=2)[N:18]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[N:17]=1.CCN(CC)CC>C(Cl)Cl.O>[CH:12]([CH:13]1[CH2:15][CH:14]1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]#[N:26])[CH:23]=2)[N:18]([S:27]([C:30]2[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=2)(=[O:28])=[O:29])[N:17]=1)=[O:11]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22638704HCID 22638704, compound

Product 1

HCID 22638715HCID 22638715, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Anhydrous DMSO (0.20 mL, 2.8 mmol) was added dropwise to a solution of oxalyl chloride (0.21 mL, 2.4 mmol) in 20 mL anhydrous CH2Cl2 under N2 at −78° C. and stirred for 30 min. A solution of 3-(2-hydroxymethyl-cyclopropyl)-1-(toluene-4-sulfonyl)-1H-indazole-5-carbonitrile (634 mg, 1.63 mmol) in 20 mL anhydrous CH2Cl2 was then added and stirring continued for 40 min. at −78° C. Et3N (1.25 mL, 8.98 mmol) was added and stirring continued for 10 min at −78° C. The reaction was warmed to room temperature and 25 mL water was added. The layers were partitioned, and the aqueous layer was extracted with CH2Cl2. The organic layers were pooled, extracted with brine, and dried over MgSO4, and concentrated in vacuo to give 3-(2-formyl-cyclopropyl)-1-(toluene-4-sulfonyl)-1H-indazole-5-carbonitrile (637 mg, 100%). 1H NMR (500 MHz, CDCl3) 9.54 (1H, d, J=3.66 Hz), 8.20 (1H, d, J=8.85 Hz), 8.05 (1H, s), 7.83 (2H, d, J=8.24 Hz), 7.77 (1H, dd, J=8.85, 1.53 Hz), 7.29 (2H, d, J=8.24 Hz), 2.82 (1H, m), 2.62(1H, m), 2.39 (3H, s), 1.82 (2H, m).

Workup

  1. stirringstirring
  2. waitcontinued for 40 min. at −78° C
  3. stirringstirring
  4. waitcontinued for 10 min at −78° C
  5. customThe layers were partitioned
  6. extractionthe aqueous layer was extracted with CH2Cl2
  7. extractionextracted with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05b5c8de766b4a2ab3ed0f3a078cb6ad
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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