Dimethyl Sulfoxide → HCID 89462933, compound

HRID 1473226Notes

Reaction equation

HRID 1473226 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[C:22]2[C:23](=[O:41])[N:24]([CH3:40])[C:25]([CH2:38][OH:39])=[C:26]([C:27]3[C:28]([CH3:37])=[C:29]4[C:34](=[CH:35][CH:36]=3)[O:33][CH2:32][CH2:31][CH2:30]4)[C:21]=2[CH:20]=[CH:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([N:18]1[C:22]2[C:23](=[O:41])[N:24]([CH3:40])[C:25]([CH:38]=[O:39])=[C:26]([C:27]3[C:28]([CH3:37])=[C:29]4[C:34](=[CH:35][CH:36]=3)[O:33][CH2:32][CH2:31][CH2:30]4)[C:21]=2[CH:20]=[CH:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 89473308HCID 89473308, compound

Product 1

HCID 89462933HCID 89462933, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A −78° C. solution of oxalyl chloride (1.816 mL, 20.75 mmol) in Dichloromethane (DCM) (40.0 mL) was treated slowly with DMSO (2.94 mL, 41.5 mmol) and the resultant was stirred at −78° C. for 15 minutes. A solution of 1-benzyl-5-(hydroxymethyl)-6-methyl-4-(5-methylchroman-6-yl)-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (5.1 g, 9.84 mmol) in Dichloromethane (DCM) (40.0 mL) was slowly added and the mixture was stirred at −78° C. for 40 minutes. Triethylamine (11.57 mL, 83 mmol) was then added and the mixture was stirred at −78° C. for 6 hours. The mixture was quenched with saturated sodium bicarbonate and then extracted with dichloromethane. The combined extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (0-100% ethyl acetate/hexanes) to give 1-benzyl-6-methyl-4-(5-methylchroman-6-yl)-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridine-5-carbaldehyde (1.53 g, 3.71 mmol, 35.8% yield). 1H NMR (400 MHz, CHLOROFORM-d) ppm 9.45 (s, 1H), 7.41-7.24 (m, 5H), 7.06 (m, 1H), 6.99 (d, J=8.2 Hz, 1H), 6.75 (d, J=8.2 Hz, 1H), 6.02 (d, J=2.9 Hz, 1H), 6.00-5.93 (m, 1H), 5.88-5.78 (m, 1H), 4.21 (t, J=5.0 Hz, 2H), 3.95 (s, 3H), 2.70 (t, J=6.4 Hz, 2H), 2.18-2.07 (m, 2H), 1.98 (s, 3H); LC/MS (m/z) ES+=413 (M+1).

Workup

  1. stirringthe mixture was stirred at −78° C. for 40 minutes
  2. stirringthe mixture was stirred at −78° C. for 6 hours
  3. customThe mixture was quenched with saturated sodium bicarbonate
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3f53bbe698f54a0c81390316a99e9d0a
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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