N-Iodosuccinimide → 5-Iodo-2,3-dihydrobenzofuran-6-amine

HRID 521592Notes

Reaction equation

HRID 521592 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([NH2:10])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.C1C(=O)N([I:18])C(=O)C1>C(#N)C>[I:18][C:8]1[C:7]([NH2:10])=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 123690442,3-Dihydro-1-benzofuran-6-amine

Product 1

HCID 671156155-Iodo-2,3-dihydrobenzofuran-6-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,3-dihydrobenzofuran-6-amine (S6-1; 95 mg, 0.7 mmol) in acetonitrile (3 mL) cooled in an ice-bath was added NIS (158 mg, 0.7 mmol). After stirring at 0° C. for 20 min, the mixture was condensed and purified by flash chromatography (hexane:EtOAc, 90:10 to 20:80) to yield S7-1 (180 mg, 98%) as a yellow solid. 1H NMR (500 MHz, CDCl3) δ 7.38 (s, 1H), 6.26 (s, 1H), 4.53 (t, J=8.5 Hz, 2H), 3.09 (t, J=8.4 Hz, 2H); MS (ESI) m/z 261.9 [M+H]+.

Workup

  1. customcondensed
  2. custompurified by flash chromatography (hexane:EtOAc, 90:10 to 20:80)
  3. customto yield S7-1 (180 mg, 98%) as a yellow solid

Sources & evidence

ORD record
ord-73fe4859e6bc44cda8834acbade66134
Source dataset
uspto-grants-2016_05
Patent number
US09328114B2

Reaction notes

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