Isopropanol → HCID 19040771, compound

HRID 1683917Notes

Reaction equation

HRID 1683917 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17].Cl[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21](Cl)[N:20]=1.[H-].[Na+].[CH3:31][CH:32]([OH:34])[CH3:33]>>[CH:32]([O:34][C:21]1[N:20]=[C:19]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH3:17])[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=1)([CH3:33])[CH3:31]

Participants

5

Reactant 4

HCID 3776Isopropanol2×HCID 24758Sodium hydrideHCID 852392,6-Dichloro-3-nitropyridineHCID 10376533(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Product 1

HCID 19040771HCID 19040771, compoundYield 42%

Procedure

(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole and 2,6-dichloro-3-nitropyridine were used. No base was used, and 2-propanol was used as solvent. This reaction mixture was stirred at room temperature was 1 hour. Then a solution of sodium hydride (5 eq) in 2-propanol was added dropwise to the above reaction mixture with cooling at 0° C. The resulting reaction mixture was stirred at room temperature under nitrogen for 2.5 hours. The reaction mixture was then evaporated under reduced pressure. Column chromatography of the residue afforded the title compound (42%) as an orange amorphous solid: 1H NMR (CDCl3) δ10.6 (br s, NH), 8.57 (br s, NH), 8.37 (d, J=9.2 Hz, 1H), 7.71 (s, 1H), 7.34-7.28 (m, 2H), 7.05 (d, J=2.0 Hz, 1H), 6.08 (d, J=9.2 Hz, 1H), 5.14 (sept, J=6.2 Hz, 1H), 3.18-3.10 (m, 2H), 2.61 (dd, J=14.0 and 9.4 Hz, 1H), 2.54-2.45 (m, 1H), 2.44 (s, 3H), 2.23 (dd, J=17.2 and 9.3 Hz, 1H), 1.90-1.53 (m, 4H), 1.25 (d, J=6.1 Hz, 3H), 1.24 (d, J=6.2 Hz, 3H); 13C NMR (CDCl3) δ166.3, 151.8, 138.1, 134.1, 129.5, 127.9, 123.1, 121.7, 119.2, 114.2, 113.9, 111.0, 102.8, 70.4, 66.4, 57.5, 40.8, 31.5, 29.9, 21.9, 14.0, 11.0; FAB HRMS calculated for [C22H27N5O3.H]410.2194, found 409.2187.

Workup

  1. temperaturewith cooling at 0° C
  2. customThe resulting reaction mixture
  3. stirringwas stirred at room temperature under nitrogen for 2.5 hours
  4. customThe reaction mixture was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-de54064bae734e2e81af0fded85322cf
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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