Water → HCID 58215837, compound

HRID 1661596Notes

Reaction equation

HRID 1661596 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[CH:7]2.Br[CH2:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=1.O>CS(C)=O>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[C:8]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[CH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 12011261HCID 12011261, compound

Product 1

HCID 58215837HCID 58215837, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A flask is charged with NaH (0.284 g, 7.093 mmol) and DMSO (1.5 mL). 5-Fluoro-2-pyridin-3-yl-indole (Example 7, 0.112 g, 0.507 mmol) in DMSO (0.5 mL) is added. The flask and syringes are rinsed with DMSO (2 times 0.5 mL). After 10 min, ethyl 4-(bromomethyl)benzoate (0.192 g, 0.760 mmol) is added neat. After 10 min, water is added. The resulting precipitate is filtered through a sintered funnel and washed with water and dichloromethane to give 4-(5-fluoro-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid as an off-white solid. 1H NMR (400 MHz, MeOD) δ ppm (sodium salt) 5.49 (s, 2H), 6.77 (s, 1H), 6.92 (d, J=8.1 Hz, 2H), 6.95-7.00 (m, 1H), 7.31-7.37 (m, 2H), 7.49 (dd, J=7.7, 5.2 Hz, 1H), 7.85 (d, J=8.1 Hz, 2H), 7.87-7.92 (m, 1H), 8.56 (dd, J=4.9, 1.5 Hz, 1H), 8.68 (d, J=1.5 Hz, 1H). HRMS (ESI) m/z 347.1212 [(M+H)+ Calcd for C21H16FN2O2: 347.1196].

Workup

  1. washThe flask and syringes are rinsed with DMSO (2 times 0.5 mL)
  2. waitAfter 10 min
  3. filtrationThe resulting precipitate is filtered through a sintered funnel
  4. washwashed with water and dichloromethane

Sources & evidence

ORD record
ord-2319926adb6146cbac23b499983673dd
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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