Dimethyl Sulfoxide → HCID 67044738, compound

HRID 2367094Notes

Reaction equation

HRID 2367094 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:25]=[CH:24]2)[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16].C(N(CC)CC)C>ClCCl>[CH3:35][Si:34]([CH3:37])([CH3:36])[CH2:33][CH2:32][O:31][CH2:30][N:26]1[C:27]2[C:23](=[CH:22][C:21]([C:12]([C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]#[N:16])=[O:11])=[CH:29][CH:28]=2)[CH:24]=[CH:25]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67044786HCID 67044786, compound

Product 1

HCID 67044738HCID 67044738, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of oxalyl chloride (0.097 mL, 1.1 mmol) in dichloromethane cooled to −60° C. was added dimethyl sulfoxide (0.16 mL, 2.2 mmol), followed by 2-{hydroxy[1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indol-5-yl]methyl}benzonitrile (0.21 g, 0.55 mmol in 2 mL dichloromethane). Triethylamine (0.46 mL, 3.3 mmol) was added and the solution was allowed to warm to room temperature and stirred for 30 min. The reaction mixture was quenched with an excess of water, and diluted with dichloromethane and brine. The layers were separated, and the aqueous layer was extracted (2×100 mL dichloromethane), dried (sodium sulfate), filtered and concentrated in vacuo. Column chromatography (silica gel, 4:1 hexanes/ethyl acetate) gave 0.12 g (58%) of 2-{[1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indol-5-yl]carbonyl}benzonitrile. 1H NMR (400 MHz, CDCl3): 8.07 (d, 1H), 7.88 (dd, 2H), 7.70 (m, 3H), 7.60 (d, 1H), 7.30 (d, 1H), 6.65 (m, 1H), 5.56 (s, 2H), 3.53 (m, 2H), 0.95 (m, 2H), 0.00 (s, 9H); 13C NMR (400 MHz, CDCl3): 194.90 (C═O), 144.16, 140.45, 135.12, 133.07, 131.72, 131.03, 130.81, 129.82, 129.66, 127.08, 125.30, 118.39, 112.98, 111.50, 105.56, 77.05, 67.48, 19.09, 0.00.

Workup

  1. customThe reaction mixture was quenched with an excess of water
  2. additiondiluted with dichloromethane and brine
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted (2×100 mL dichloromethane)
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ea33e12c477463b849452d4f1bd9c23
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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