Sodium Iodide → HCID 67196837, compound

HRID 1013022Notes

Reaction equation

[CH:1]([C:9]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[N:12]=[C:11]([C:21]([F:24])([F:23])[F:22])[CH:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:26][CH2:27][CH2:28][N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.[H-].[Na+].[I-].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[N:29]1([CH2:28][CH2:27][CH2:26][O:20][C:17]2[CH:18]=[CH:19][C:14]([N:13]3[C:9]([CH:1]=[CH:2][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)=[CH:10][C:11]([C:21]([F:24])([F:23])[F:22])=[N:12]3)=[CH:15][CH:16]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

Conditions

Temperature: 70 °C

Procedure

4-(5-Styryl-3-trifluoromethylpyrazol-1-yl)phenol (0.2 mmol) was dissolved in N,N-dimethylformamide (1 mL), and 1-(3-chloropropyl)pyrrolidine (32 mg, 0.22 mmol), sodium hydride (9 mg, 60% dispersion in mineral oil, 0.22 mmol) and sodium iodide (33 mg, 0.22 mmol) were added. The reaction was heated at 70° C. overnight, 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. Semi-prep LC-MS purification gave 20.8 mg of the desired product. LC-MS (C25H26F3N3O calculated 441) m/z 442 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.42-7.30 (m, 7H), 7.12 (d, J=16.2 Hz, 1H), 7.00 (d, J=8.7 Hz, 2H), 6.88 (s, 1H), 6.77 (d, J=16.5 Hz, 1H), 4.10 (t, J=6 Hz, 2H), 2.93-2.86 (m, 6H), 2.21-2.12 (m, 2H), 1.94-1.90 (m, 4H).

Workup

temperaturecooled to room temperature
extractionthe mixture was extracted with ethyl acetate
dry with materialThe extracts were dried over MgSO4
concentrationconcentrated
customSemi-prep LC-MS purification

Sources & evidence

ORD record: ord-066a65c08c0b4541a34d835c8f061689
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981896B2

Reaction notes

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