Potassium Iodide → HCID 90417450, compound

HRID 718137Notes

Reaction equation

HRID 718137 reaction equation
N[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]([NH:17][CH3:18])=[O:16])[CH:10]=2)=[CH:4][CH:3]=1.[I-:19].[K+].C(ON=O)(C)(C)C>C(I)I.CCOC(C)=O>[I:19][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]([NH:17][CH3:18])=[O:16])[CH:10]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 10906Tert-Butyl nitriteHCID 90410540HCID 90410540, compound

Product 1

HCID 90417450HCID 90417450, compoundYield 36.8%

Reagents, catalysts & solvents 2

HCID 6346DiiodomethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-((6-aminopyridin-3-yl)oxy)-N-methylpicolinamide (0.4 g, 1.64 mmol) and potassium iodide (1.36 g, 8.19 mmol) in methylene iodide (5.46 mL) was treated dropwise with t-butylnitrite (1.95 mL, 16.4 mmol). The mixture was stirred overnight at RT, diluted with EtOAc (75 mL), and washed with 10% sodium carbonate (50 mL), 10% thiosulfate (50 mL), and brine (50 mL). The organics were dried over sodium sulfate, evaporated to dryness and purified by silica gel chromatography ((EtOAc/Hex) to afford 4-((6-iodopyridin-3-yl)oxy)-N-methylpicolinamide (0.214 g, 36.8%). 1H NMR (400 MHz, DMSO-d6): δ 8.78 (br d, J=5.6 Hz, 1H), 8.54 (d, J=5.6 Hz, 1H), 8.40 (d, J=3.0 Hz, 1H), 7.95 (d, J=8.6 Hz, 1H), 7.50 (dd, J=8.6, 3.1 Hz, 1H), 7.45 (d, J=2.6 Hz, 1H), 7.23 (dd, J=5.6, 2.7 Hz, 1H), 2.78 (d, J=4.9 Hz, 3H); MS (ESI) m/z: 356.0 (M+H+).

Workup

  1. washwashed with 10% sodium carbonate (50 mL), 10% thiosulfate (50 mL), and brine (50 mL)
  2. dry with materialThe organics were dried over sodium sulfate
  3. customevaporated to dryness
  4. custompurified by silica gel chromatography ((EtOAc/Hex)

Sources & evidence

ORD record
ord-722e9a26c4ce47dbb1b2690bdfcf1934
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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