Triethylamine → HCID 89422916, compound

HRID 1481740Notes

Reaction equation

HRID 1481740 reaction equation
[CH3:1][O:2][C:3]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:4]=1[CH2:5][N:6]1[C:11]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16]([CH2:22][CH2:23][OH:24])=[CH:15]3)=[C:10]([CH2:25][CH3:26])[CH:9]=[C:8]([C:27]([O:29][CH3:30])=[O:28])[C:7]1=[O:31].CCN(CC)CC.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:4]=1[CH2:5][N:6]1[C:11]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16]([CH2:22][CH2:23][O:24][S:46]([CH3:45])(=[O:48])=[O:47])=[CH:15]3)=[C:10]([CH2:25][CH3:26])[CH:9]=[C:8]([C:27]([O:29][CH3:30])=[O:28])[C:7]1=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71284985HCID 71284985, compound

Product 1

HCID 89422916HCID 89422916, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To solution of methyl 1-(2,4-dimethoxybenzyl)-5-ethyl-6-(2-(2-hydroxyethyl)-1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate (1.142 g, 2.26 mmol) in DCM (10 mL) was added NEt3 (0.45 mL, 3.23 mmol) and mixture was cooled to 0° C. Methanesulfonyl chloride (0.22 mL, 2.84 mmol) was added dropwise and reaction mixture was stirred at 0° C. 15 min. LC/MS indicated complete consumption of the starting material. Reaction was diluted with DCM (20 mL) and washed with H2O (10 mL). Organic phase was dried over Na2SO4 and solvent was removed under reduced pressure. Methyl 1-(2,4-dimethoxybenzyl)-5-ethyl-6-(1-methyl-2-(2-(methylsulfonyloxy)ethyl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate (1.30 g) was obtained in nearly quantitative yield as yellow solid and was pure enough to be used in the next step without purification.

Workup

  1. customreaction mixture
  2. custom15 min
  3. customconsumption of the starting material
  4. customReaction
  5. washwashed with H2O (10 mL)
  6. dry with materialOrganic phase was dried over Na2SO4 and solvent
  7. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-0aa894561659414b9d6a9217d68655f4
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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