Sodium Iodide → 8-Methoxy-3-methyl-1-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-4,5-dihydro-1H-benzo[g]indazole

HRID 1013029Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[CH2:7][CH2:8][C:9]3[C:10]([CH3:21])=[N:11][N:12]([C:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=4)[C:13]=3[C:5]=2[CH:4]=1.Cl[CH2:25][CH2:26][CH2:27][N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.[H-].[Na+].[I-].[Na+]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[CH2:7][CH2:8][C:9]3[C:10]([CH3:21])=[N:11][N:12]([C:14]4[CH:19]=[CH:18][C:17]([O:20][CH2:25][CH2:26][CH2:27][N:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)=[CH:16][CH:15]=4)[C:13]=3[C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

4-(8-Methoxy-3-methyl-4,5-dihydrobenzo[g]indazol-1-yl)-phenol (0.1 mmol) was dissolved in N,N-dimethylformamide (1 mL), and -(3-chloropropyl)pyrrolidine (15 mg, 0.1 mmol), sodium hydride (4 mg, 60% dispersion in mineral oil, 0.1 mmol) and sodium iodide (15 mg, 0.1 mmol) were added. The reaction was heated at 70° C. for 3 hours. The solution was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were dried over MgSO4 and concentrated. SiO2 chromatography with 2% triethylamine/10% methanol/ethyl acetate gave 8.6 mg of the desired product. LC-MS (C26H31N3O2 calculated 417) m/z 418 (M+H). 1H NMR (300 MHz, CDCl3) δ 7.41-7.36 (m, 2H), 7.17 (d, J=8.7 Hz, 1H), 6.99-6.94 (m, 2H), 6.67 (dd, J=8.7 Hz, 2.4 Hz, 1H), 6.40 (d, J=2.4 Hz, 1H), 4.07 (t, J=6.3 Hz, 2H), 3.52 (s, 3H), 2.91 (m, 2H), 2.72-2.58 (m, 8H), 2.30 (s, 3H), 2.12-2.04 (m, 2H), 1.86-1.81 (m, 4H).

Workup

extractionextracted with ethyl acetate
dry with materialThe extracts were dried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-78dfd8450c634412b88414a3c26533da
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981896B2

Reaction notes

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