Water → HCID 136123733, compound

HRID 1850279Notes

Reaction equation

HRID 1850279 reaction equation
Cl[C:2]1[C:3]([CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[OH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>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]>[C:15]([O:14][C:12]([N:10]1[CH2:11][CH:8]([C:3]2[C:2]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[OH:19])=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 2773454(2-Hydroxyphenyl)boronic acidHCID 59351411Tert-butyl 3-(3-chloropyrazin-2-yl)azetidine-1-carboxylate

Product 1

HCID 136123733HCID 136123733, compoundYield 92%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

To a solution of 3-(3-chloro-pyrazin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (7) (540 mg, 2.0 mmol, see Preparation 2), 2-hydroxy-phenylboronic acid (71) (303.6 mg, 2.2 mmol), K3PO4 (818 mg, 4.0 mmol), in dioxane (20 mL) and water (4 mL) was added Pd(dppf)Cl2 (73.2 mg, 0.1 mmol) then the reaction mixture was stirred at 90° C. under nitrogen atmosphere overnight. The reaction mixture was filtered through CELITE® and washed with EtOAc (50 mL). The filtrate was concentrated and the crude product was purified by silica gel column to give (72) (601.7 mg, 1.84 mmol, yield 91.85%).

Workup

  1. filtrationThe reaction mixture was filtered through CELITE®
  2. washwashed with EtOAc (50 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe crude product was purified by silica gel column

Sources & evidence

ORD record
ord-23a5ed2311e14cd1ad14bbf0c19a1106
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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