Triethylamine → HCID 57949692, compound

HRID 2427526Notes

Reaction equation

HRID 2427526 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[C:16]([CH3:18])[CH:17]=2)[C:14](=[O:19])[N:13]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)[CH2:12]3)[CH:6]=[N:7][CH:8]=1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>ClCCl>[CH3:18][C:16]1[CH:17]=[C:9]([C:5]2[CH:4]=[C:3]([CH2:2][O:1][S:40]([CH3:39])(=[O:42])=[O:41])[CH:8]=[N:7][CH:6]=2)[CH:10]=[C:11]2[C:15]=1[C:14](=[O:19])[N:13]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][C:28]([F:30])([F:31])[F:29])=[CH:25][CH:26]=1)[CH2:12]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57949591HCID 57949591, compound

Product 1

HCID 57949692HCID 57949692, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-(5-Hydroxymethyl-pyridin-3-yl)-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (72 mg, 0.168) was diluted with dichloromethane (5 mL) and the solution was cooled to 0° C. in an icebath. Triethyl amine (47 μL, 0.168 mmol) and methanesulfonyl chloride (19 μL, 0.252 mmol) were added and stirring continued for 1 hr at 0° C. The mixture was quenched with cold saturated sodium bicarbonate and the organics were dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound as black oil (70 mg, 100%). 1H NMR (300 MHz, CDCl3): δ 8.01 (s, 1H), 7.43-7.37 (m, 5H), 7.23-7.20 (m, 3H), 5.37 (s, 2H), 4.83 (s, 2H), 4.34 (s, 2H), 3.09 (s, 3H), 2.86 (s, 3H).

Workup

  1. customThe mixture was quenched with cold saturated sodium bicarbonate
  2. dry with materialthe organics were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bf793e4cd3174f14a7b6abb16120324d
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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