Isopropyl iodide → HCID 24995281, compound

HRID 423706Notes

Reaction equation

HRID 423706 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]4[NH:29][N:28]=[N:27][N:26]=4)[CH2:21][CH2:20]3)=[CH:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].I[CH:37]([CH3:39])[CH3:38]>CN(C=O)C.CC(C)=O>[CH3:38][CH:37]([N:27]1[N:28]=[N:29][C:25]([N:22]2[CH2:23][CH2:24][CH:19]([CH2:18][O:17][C:14]3[CH:15]=[CH:16][C:11]([C:8]4[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=4)=[N:12][CH:13]=3)[CH2:20][CH2:21]2)=[N:26]1)[CH3:39]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178504673HCID 178504673, compound

Product 1

HCID 24995281HCID 24995281, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-[4-(methylsulfonyl)phenyl]-5-({[1-(1H-tetrazol-5-yl)-4-piperidinyl]methyl}oxy)pyridine (157 mg, 0.38 mmol) in DMF (2 mL) and acetone (3 mL) was added potassium carbonate (105 mg, 0.76 mmol) at room temperature. After stirring for 15 min, 2-iodopropane (193 mg, 1.14 mmol) was added by syringe and the mixture was heated at 50° C. for 16 h. The salt was removed by filtration and washed with MeOH/CH2Cl2. After concentration, a small amount of MeOH/CH2Cl2 was added and the resulting precipitate was collected and washed with a small amount of MeOH. The material was dried in vacuo to give the title compound (130 mg, 71%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.44 (d, 1H, J=2.9 Hz), 8.34-8.25 (m, 2H), 8.07 (d, 1H, J=8.8 Hz), 7.99 (d, 2H, J=8.7 Hz) 7.55 (dd, 1H, Ja=8.8 Hz, Jb=2.9 Hz), 4.88 (septet, 1H, J=6.7 Hz), 4.03 (d, 2H, J=6.6 Hz), 3.98 (d, 2H, J=12.6 Hz), 3.25 (s, 3H), 3.01-2.86 (m, 2H), 2.11-1.95 (m, 1H), 1.94-1.82 (m, 2H), 1.50 (d, 6H, J=6.7 Hz), 1.46-1.30 (m, 2H); LRMS (ESI), m/z 457 (M+H).

Workup

  1. customThe salt was removed by filtration
  2. washwashed with MeOH/CH2Cl2
  3. concentrationAfter concentration
  4. additiona small amount of MeOH/CH2Cl2 was added
  5. customthe resulting precipitate was collected
  6. washwashed with a small amount of MeOH
  7. customThe material was dried in vacuo

Sources & evidence

ORD record
ord-654a5ba5da98453b9c36c0c96111b389
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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