Diisopropylethylamine → N-(5-iodopyridin-2-yl)-2-(4-(2-methylpyridin-4-yl)phenyl)acetamide

HRID 1036184Notes

Reaction equation

HRID 1036184 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=O)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[I:18][C:19]1[CH:20]=[CH:21][C:22]([NH2:25])=[N:23][CH:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[I:18][C:19]1[CH:20]=[CH:21][C:22]([NH:25][C:15](=[O:17])[CH2:14][C:11]2[CH:10]=[CH:9][C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=3)=[CH:13][CH:12]=2)=[N:23][CH:24]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 885792-Pyridinamine, 5-iodo-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58447644[4-(2-Methyl-pyridin-4-yl)-phenyl]-acetic acid

Product 1

HCID 58447796N-(5-iodopyridin-2-yl)-2-(4-(2-methylpyridin-4-yl)phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-(2-methylpyridin-4-yl)phenyl)acetic acid 65-1 (300 mg, 1.3 mmol), 5-iodopyridin-2-amine (344 mg, 1.6 mmol) and HATU (590 mg, 1.6 mmol) in DMF (8 mL) was added DIEA (503 mg, 3.9 mmol) at room temperature. After stirred at room temperature for 2 hours, the reaction mixture was diluted into ethyl acetate and washed with saturated NaHCO3 solution and then brine. The organic phase was dried over MgSO4. The solvent was removed and the crude product was purified by silica gel flash chromatography to afford N-(5-iodopyridin-2-yl)-2-(4-(2-methylpyridin-4-yl)phenyl)acetamide 65-2 as off-white solid. MS m/z 430.1 (M+1).

Workup

  1. washwashed with saturated NaHCO3 solution
  2. dry with materialThe organic phase was dried over MgSO4
  3. customThe solvent was removed
  4. customthe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-d529d8905133428b874e3d905a44bac8
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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