Iodoethane → Bet-IN-36

HRID 575575Notes

Reaction equation

HRID 575575 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]([OH:30])=[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:20]=3)[C:15](=[O:28])[N:14]([CH3:29])[CH:13]=2)[CH:11]=1)(=[O:5])=[O:4])[CH3:2].[CH2:31](I)[CH3:32].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:31]([O:30][C:9]1[CH:8]=[CH:7][C:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])=[CH:11][C:10]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]3[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=3)[CH:20]=2)[C:15](=[O:28])[N:14]([CH3:29])[CH:13]=1)[CH3:32]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 118021404US10023592, Example 80

Product 1

HCID 118021718Bet-IN-36Yield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the title compound of Example 80 (25.0 mg, 0.059 mmol), ethyl iodide (27.7 mg, 0.177 mmol), and K2CO3 (24.5 mg, 0.177 mmol) in acetone (2 mL) was stirred at room temperature for 18 h. After CH2Cl2 extractive work up, purification by preparative TLC (PE:EA=2:1) gave the title compound (15.8 mg, 60%) as a white solid. 1H NMR: (CDCl3, 400 MHz) δ 8.48 (d, J=8.4 Hz, 1H), 7.97 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.86 (d, J=2.4 Hz, 1H), 7.68 (s, 1H), 7.62 (s, 1H), 7.61 (dd, J1=8.4 Hz, J2=1.6 Hz, 1H), 7.17 (d, J=1.2 Hz, 1H), 7.15 (d, J=8.4 Hz, 1H), 7.08 (s, 1H), 4.3 (q, J=7.2 Hz, 2H), 3.94 (s, 3H), 3.66 (s, 3H), 3.17 (q, J=7.6 Hz, 2H), 1.35 (t, J=7.6 Hz, 3H), 1.18 (t, J=7.2 Hz, 3H). LCMS: 452.1 (M+H)+

Workup

  1. customAfter CH2Cl2 extractive work up, purification by preparative TLC (PE:EA=2:1)

Sources & evidence

ORD record
ord-6040145114d14eb89e9d30facb8fc508
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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