Sodium hydride → HCID 19601673, compound

To a solution of 1-(3-iodophenyl)-N-methyl-3-isoquinolinecarboxamide (22 mg, 0.06 mmol) in DMF (4.6 mL) was added 60% NaH (16 mg, 0.39 mmol) in one portion. The mixture was stirred under Ar at room temperature for 15 min. Then, 3-fluoropropyl bromide (29 μl, 0.39 mmol) was added. After stirring at room temperature for 20 h, the mixture was quenched by adding H2O (5 mL). The mixture was extracted with CH2Cl2 (3×15 mL). The combined organic layers were dried (MgSO4), filtered. The filtrate was concentrated in vacuo. The residue was chromatographed (SiO2, 30% ethyl acetate/hexane, 0.035% Et3N), thereby affording a semisolid (4.4 mg, 37%). 1H NMR (CDCl3) d 2.04-2.24 (m, 2 H, CH2), 3.16, 3.18 (two s, total 3 H, N-methyl), 3.60-3.75 (m, 2 H, N--CH2), 4.25-4.70 (qt, J=67.8, 47.1, 5.7 Hz, 2 H, CH2F), 7.20-7.30 (m, 1 H, aromatic), 7.55-7.65 (m, 2 H, aromatic), 7.73 (t, J=7.2 Hz, 1 H, aromatic), 7.83 (d, J=7.8 Hz, 1 H, aromatic), 7.94 (d, J=8.4 Hz, 1 H, aromatic), 7.98-8.09 (m, 2 H, aromatic), 8.12 (s, 1 H, aromatic). HRMS calcd. for C20H18FIN2O: 448.0448. Found: 448.0461

1. stirringAfter stirring at room temperature for 20 h
2. customthe mixture was quenched
3. additionby adding H2O (5 mL)
4. extractionThe mixture was extracted with CH2Cl2 (3×15 mL)
5. dry with materialThe combined organic layers were dried (MgSO4)
6. filtrationfiltered
7. concentrationThe filtrate was concentrated in vacuo
8. customThe residue was chromatographed (SiO2, 30% ethyl acetate/hexane, 0.035% Et3N)

ORD record

ord-ba59c4aeddeb4d8a8e900ec818b2c5ef

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998624