Potassium Carbonate → (3-(1-isopropyl-1H-pyrazol-5-yl)pyridin-4-yl)methanol

HRID 1471715Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].[CH:10]([N:13]1[C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][CH:15]=[N:14]1)([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+].O1CCOCC1>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].O>[CH:10]([N:13]1[C:17]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[CH2:8][OH:9])=[CH:16][CH:15]=[N:14]1)([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of (3-bromopyridin-4-yl)methanol (150 mg, 0.8 mmol, 1 eq.), 1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (226 mg, 0.96 mmol, 1.2 eq.), Pd(dppf)Cl2 (58 mg, 0.08 mmol, 0.1 eq.), and K2CO3 (331 mg, 3.0 mmol, 3 eq.) in a RB flask were added dioxane (6 mL) and water (2 mL). The mixture was heated at 100° C. for 2 h, cooled, filtered, and concentrated. The crude was purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-(1-isopropyl-1H-pyrazol-5-yl)pyridin-4-yl)methanol (75 mg, 43%) as a yellow oil. LRMS (M+H+) m/z 218.1.

Workup

temperaturecooled
filtrationfiltered
concentrationconcentrated
customThe crude was purified on silica gel using
additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record: ord-bc0aaf9afc144d0c9d82e70c4ac50ce0
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012450B2

Reaction notes

Loading…