Diethyl Ether → HCID 131734299, compound

HRID 1502163Notes

Reaction equation

Br[C:2]1[N:7]=[N:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[Cl-].[C:50]([O:54][C:55](=[O:58])[CH2:56][Zn+])([CH3:53])([CH3:52])[CH3:51].C(OCC)C>CCOC(C)=O>[C:9]([NH:8][C:5]1[N:6]=[N:7][C:2]([CH2:56][C:55]([O:54][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:58])=[CH:3][CH:4]=1)(=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of N-(6-bromopyridazin-3-yl)pivalamide (2.00 g, 7.75 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.222 g, 0.465 mmol), and tris-dipalladium(dibenzylideneacetone) (0.213 g, 0.232 mmol) was flushed with nitrogen for 30 min. THF (20 mL) was added, followed by a 1.0 M solution of (2-tert-butoxy-2-oxoethyl)zinc(II) chloride in diethyl ether (38.7 mL, 19.4 mmol) and the reaction was sealed and stirred for 2 h at 50° C. An additional amount of (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (15.5 ml, 7.75 mmol) was added and the mixture stirred for 2 h at 50 C. The resulting mixture was diluted with EtOAc and filtered, then washed with water and brine. The organic layer was dried (sodium sulfate), filtered and concentrated. MPLC (3−>30% EtOAc:Hex) provided title compound. LC-MS (IE, m/z): 294 [M+1]+.

Workup

customwas flushed with nitrogen for 30 min
additionTHF (20 mL) was added
customthe reaction was sealed
stirringthe mixture stirred for 2 h at 50 C
filtrationfiltered
washwashed with water and brine
dry with materialThe organic layer was dried (sodium sulfate)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-4f078dc367334a2483a66a079d667607
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206199B2

Reaction notes

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