Sodium Iodide → HCID 24784311, compound

HRID 598759Notes

Reaction equation

HRID 598759 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-189ee3c27f0348c98d50465e8fe84ede
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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