(3-Fluoro-5-methoxyphenyl)boronic acid → HCID 178492931, compound

HRID 634418Notes

Reaction equation

HRID 634418 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:12][C:13]1[CH:14]=[C:15]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[NH2:11])[NH:4][N:3]=2)[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1

Participants

5

Reactant 2

HCID 2763243(3-Fluoro-5-methoxyphenyl)boronic acidHCID 178508725HCID 178508725, compound

Product 1

HCID 178492931HCID 178492931, compoundYield 18.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1.52 g, 5.82 mmol), 3-fluoro-5-methoxyphenylboronic acid (1.4 g, 8.24 mmol), Pd(dppf)Cl2 (0.18 g, 0.246 mmol) and 8.7 mL of 1M NaOHaqueous (8.73 mmol) were reacted in DMF (13 mL) under Ar at 120° C. for 48 hrs. The reaction was quenched by the addition of 1M HClaqueous (10 mL), dried under reduced pressure and the dark crude oil purified via flash chromatography on silica gel using a Biotage 100G SNAP with a gradient of DCM and iPrOH to give the title compound (275 mg, 18.2%) as yellowish solid.

Workup

  1. customThe reaction was quenched by the addition of 1M HClaqueous (10 mL)
  2. customdried under reduced pressure
  3. customthe dark crude oil purified via flash chromatography on silica gel using a Biotage 100G SNAP with a gradient of DCM and iPrOH

Sources & evidence

ORD record
ord-4a36f1540a4b4a8aa859cbc4373587e0
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

Loading…