Sodium Iodide → HCID 24784311, compound

HRID 1013018Notes

Reaction equation

HRID 1013018 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][CH2:8][C:7]3[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=3[C:5]=2[N:4]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[N:3]=1.Cl[CH2:23][CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.[H-].[Na+].[I-].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C.C(OCC)(=O)C>[CH3:1][C:2]1[C:10]2[CH2:9][CH2:8][C:7]3[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=3[C:5]=2[N:4]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:23][CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:19][CH:20]=2)[N:3]=1

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 113210281-(3-Chloropropyl)-pyrrolidineHCID 58948773HCID 58948773, compound

Product 1

HCID 24784311HCID 24784311, compoundYield 40.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

4-(3-Methyl-4,5-dihydrobenzo[g]indazol-1-yl)phenol (48 mg, 0.174 mmol) was dissolved in N,N-dimethylformamide (1 mL), and 1-(3-chloropropyl)pyrrolidine (31 mg, 0.21 mmol), sodium hydride (8 mg, 60% dispersion in mineral oil, 0.21 mmol) and sodium iodide (32 mg, 0.21 mmol) were added. The reaction was heated at 70° C. for 1.5 hours, then cooled to room temperature. Saturated sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The extracts were dried over MgSO4 and concentrated. SiO2 chromatography with ethyl acetate, then 2% triethylamine/10% methanol/ethyl acetate gave 27.4 mg of the desired product (40% yield). LC-MS (C25H29N3O calculated 387) m/z 388 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.39-7.34 (m, 2H), 7.27 (d, J=7.5 Hz, 1H), 7.12 (t, J=7.5 Hz, 1H), 7.01-6.93 (m, 3H), 6.81 (d, J=7.8 Hz, 1H), 4.09 (t, J=6.3 Hz, 2H), 2.98 (t, J=6.9 Hz, 2H), 2.74-2.60 (m, 8H), 2.30 (s, 3H), 2.14-2.04 (m, 2H), 1.86-1.82 (m, 4H).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-980d4684cdc449aeb33cc4375fd612b1
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

Loading…