4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane → HCID 86674277, compound

HRID 405240Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]([CH:24]=[O:25])=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:15])=[N:12][CH:13]=2)[CH:7]=1.[CH3:26][C:27]1(C)[C:31](C)(C)OB(C(C)=C)O1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C1(C)C=CC=CC=1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:24]([C:5]1[CH:4]=[CH:3][C:2]([C:27]([CH3:31])=[CH2:26])=[CH:7][C:6]=1[C:8]1[CH:9]=[CH:10][C:11]([C:14]([NH:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:15])=[N:12][CH:13]=1)=[O:25]

Participants

Conditions

Temperature: 90 °C

Procedure

Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate (180 mg, 0.50 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (126 mg, 0.75 mmol), Pd(OAc)2 (11 mg, 0.05 mmol), S-PHOS (41 mg, 0.10) K3PO3 (318 mg, 1.50 mmol) were dissolved in toluene (2 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

temperatureAfter 16 h the resulting mixture was cooled to room temperature
washwashed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
custompurified via column chromatography

Sources & evidence

ORD record: ord-9febdb8389db48369f7d514183d6033b
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748624B2

Reaction notes

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