Potassium Acetate → HCID 71093666, compound

HRID 57571

Reaction equation

HRID 57571 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.CC1(C)C(C)(C)[O:19][B:18](B2OC(C)(C)C(C)(C)O2)[O:17]1.CC([O-])=O.[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:11]1[CH2:12][CH2:13][CH2:14][N:8]([C:5]2[N:6]=[CH:7][C:2]([B:18]([OH:19])[OH:17])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 629674864-(5-Bromopyridin-2-yl)-1,4-oxazepane

Product 1

HCID 71093666HCID 71093666, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(5-bromopyridin-2-yl)-1,4-oxazepane (600 mg, 2.33 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.18 g, 4.67 mmol), Pd(dppf)Cl2 (286 mg, 0.35 mmol) and KOAc (687 mg, 6.99 mmol) in 30 ml of dioxane, under N2, was stirred at 110° C. for 3 hours. The volatiles were removed in vacuo, and the residue was purified by chromatography with EA/MeOH (20:1˜5:1) to give 165 mg of 6-(1,4-oxazepan-4-yl)pyridin-3-ylboronic acid. MS (m/z)=223 (M+H)+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by chromatography with EA/MeOH (20:1˜5:1)

Sources & evidence

ORD record
ord-57810057821240548e70e9d197a87133
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

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