N-Iodosuccinimide → HCID 66761027, compound

HRID 389592Notes

Reaction equation

HRID 389592 reaction equation
[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]3[O:19][C:13]4=[C:14]([NH2:18])[N:15]=[CH:16][CH:17]=[C:12]4[CH:11]=3)[C:5]=12.C1C(=O)N([I:27])C(=O)C1>CN(C=O)C>[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]3[O:19][C:13]4=[C:14]([NH2:18])[N:15]=[CH:16][C:17]([I:27])=[C:12]4[CH:11]=3)[C:5]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 66760373HCID 66760373, compound

Product 1

HCID 66761027HCID 66761027, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 2-(imidazo[1,5-a]pyridin-8-yl)furo[2,3-c]pyridin-7-amine (82.0 mg, 0.328 mmol) in DMF (4 mL) was added NIS (74.0 mg, 0.329 mmol) in portions. After stirring from 0° C. to RT over 1 h, the mixture was adsorbed onto silica gel. Purification by ISCO chromatography (50 to 100% ethyl acetate:heptane and then 15% methanol:dichloromethane), followed by mass-directed purification afforded 11.7 mg (10%) of the title compound as a yellow solid. 1H NMR (400 MHz, MeOH-d4): δ 9.37 (s, 1H), 8.65 (br s, 1H), 8.62 (d, J=7.07 Hz, 1H), 8.02 (d, J=7.07 Hz, 1H), 7.98 (s, 1H), 7.64 (s, 1H), 7.23 (t, J=7.10 Hz, 1H); MS (ESI): 376.93 [M+H]+; HPLC tR=2.76 min (ZQ3: polar—5 min).

Workup

  1. customPurification by ISCO chromatography (50 to 100% ethyl acetate
  2. customheptane and then 15% methanol:dichloromethane), followed by mass-directed purification

Sources & evidence

ORD record
ord-23a88981f093400c991511edfd657b21
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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