2-Chloromethyl tetrahydrofuran → tert-Butyl 4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl((tetrahydrofuran-2-yl)methyl)carbamate

HRID 878267Notes

Reaction equation

ClC1C=CC=CC=1C1C=CN=CC=1N(CCS(C)(=O)=O)[C:15](=[O:30])[C:16]1C=C(C(F)(F)F)[CH:19]=[C:18](C(F)(F)F)[CH:17]=1.[F:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][N:47]=[CH:46][C:45]=2[NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[C:40]([O:58][CH3:59])[CH:39]=1.C(Cl)C1OCCC1>>[F:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][N:47]=[CH:46][C:45]=2[N:50]([CH2:19][CH:18]2[CH2:17][CH2:16][CH2:15][O:30]2)[C:51](=[O:57])[O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[C:40]([O:58][CH3:59])[CH:39]=1

Participants

Reactant 3

HCID 181502-Chloromethyl tetrahydrofuran

HCID 70663659HCID 70663659, compound

HCID 86670734HCID 86670734, compound

Product 1

HCID 70663625tert-Butyl 4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl((tetrahydrofuran-2-yl)methyl)carbamate

Procedure

The title compound was prepared in analogy to example 85, intermediate c, from tert-butyl 4-(4-fluoro-2-methoxyphenyl)pyridin-3-ylcarbamate and tetrahydrofurfurylchloride after a reaction time of 72 hours at 70° C. The compound was purified by silica gel chromatography on a 20 g column using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light yellow solid (38%). MS (ESI): m/z=403.205 [M+H]+.

Workup

customThe compound was purified by silica gel chromatography on a 20 g column
washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record: ord-16d268d8bd104a6e9981f35f28c46335
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987307B2

Reaction notes

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