B-[2-(Cyclopropyloxy)phenyl]boronic acid → HCID 70663294, compound

HRID 878278Notes

Reaction equation

HRID 878278 reaction equation
F[C:2]1[C:7](F)=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15]([CH2:32]CS(C)(=O)=O)C(=O)C2C=C(C(F)(F)F)N=C(C(F)(F)F)C=2)=[C:4]([O:38][CH3:39])[CH:3]=1.[CH:40]1(OC2C=CC=CC=2B(O)O)C[CH2:41]1>>[CH:39]1([O:38][C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][C:5]=2[C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[NH:15][CH3:32])[CH2:41][CH2:40]1

Participants

3

Reactant 2

HCID 18770201B-[2-(Cyclopropyloxy)phenyl]boronic acidHCID 86670771N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-(2-methanesulfonyl-ethyl)-2,6-bis-trifluoromethyl-isonicotinamide2×

Product 1

HCID 70663294HCID 70663294, compound

Conditions

Temperature
90 °C

Procedure

The title compound was prepared in analogy to example 72, from (4-iodo-pyridin-3-yl)-methyl-amine (example 36, intermediate b) and 2-cyclopropoxyphenylboronic acid after stirring at 90° C. for 18 hours. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light yellow oil (94%). MS (ESI): m/z=241.134 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-b28233aa08734abf8e5e7ba7d5c86300
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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