3-Fluoro-1-propanol → 4-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-N-(3-fluoropropyl)aniline

To 3-fluoropropan-1-ol (4 mg, 0.05 mmol) in 0.5 mL DCM was added Dess-Martin reagent (42 mg, 0.1 mmol). The mixture was stirred at rt for 1 h and filtered directly into a mixture of 4-(benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)aniline (4 mg, 0.015 mmol) and NaBH(OAc)3 (43 mg, 0.2 mmol) with stirring. After vigorously stirred for 5 min, reaction was quenched by adding 0.5 M NaOH (2 mL). The mixture was extracted with EtOAc (3×10 mL) and the organic phase was dried over MgSO4 and concentrated. The crude product was purified by HPLC to afford 4-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-N-(3-fluoropropyl)aniline as a yellow solid (2.7 mg, 33%). 1H NMR (400 MHz, CDCl3): δ 8.76 (d, J=7.2 Hz, 1H), 7.88 (m, 4H), 7.55 (d, J=7.2 Hz, 1H), 7.53 (m, 1H), 7.40 (m, 1H), 6.47 (d, J=9.2 Hz, 1H), 4.68 (t, J=5.2 Hz, 1H), 4.56 (t, J=5.2 Hz, 1H), 3.34 (t, J=6.8 Hz, 2H), 2.09 (m, 1H), 2.02 (m, 1H); MS (ESI): 321 (M+H+).

1. stirringwith stirring
2. stirringAfter vigorously stirred for 5 min
3. customreaction
4. customwas quenched
5. additionby adding 0.5 M NaOH (2 mL)
6. extractionThe mixture was extracted with EtOAc (3×10 mL)
7. dry with materialthe organic phase was dried over MgSO4
8. concentrationconcentrated
9. customThe crude product was purified by HPLC

ORD-Eintrag

ord-f79df3f3d8cf46b79c8c35ffc8733e3a

Quelldatensatz

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08691187B2