Potassium Carbonate → HCID 59128677, compound

HRID 1991111Notes

Reaction equation

HRID 1991111 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([OH:16])[CH:14]=3)[N:9]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:8]=2)[CH:4]=[N:3]1.Br[CH2:26][CH:27]1[CH2:29][CH2:28]1.C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CC(C)=O>[CH:27]1([CH2:26][O:16][C:13]2[CH:14]=[C:15]3[C:7]([C:5]4[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=4)=[CH:8][N:9]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:10]3=[N:11][CH:12]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 59128696HCID 59128696, compound

Product 1

HCID 59128677HCID 59128677, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

According to the general procedure using: 27 (60 mg, 0.174 mmol), (bromomethyl)cyclopropane (101 μL, 1.05 mmol), K2CO3 (241 mg, 1.74 mmol) and n-Bu4NI (6.4 mg, 17 μmol) in acetone (4.0 mL) were heated at reflux overnight. Standard workup and purification by PTLC using 5% MeOH in CH2Cl2 gave 28s as a clear oil (41 mg, 59%); 1H NMR (400 MHz, CDCl3) δ-0.066 (s, 9H), 0.38 (q, J=4.68 Hz, 2H), 0.68 (m, 2H), 0.91 (m, 2H), 1.31 (m, 1H), 3.55 (t, J=8.3 Hz, 2H), 3.89 (d, J=7.0 Hz, 2H), 3.98 (s, 3H), 5.64 (s, 2H), 7.36 (s, 1H), 7.51 (d, J=2.6 Hz, 1H), 7.58 (s, 1H), 7.74 (d, J=0.3 Hz, 1H), 8.16 (d, J=2.6 Hz, 1H).

Workup

  1. temperatureat reflux overnight
  2. customStandard workup and purification by PTLC

Sources & evidence

ORD record
ord-174f959d4cd84a90972e25ab9d261f62
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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