Cesium carbonate → HCID 58446992, compound

HRID 1045758Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([C:21]#[N:22])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].O1CCOCC1>[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:21]([C:4]1[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=[C:2]([C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)[N:3]=1)#[N:22]

Participants

Conditions

Temperature: 100 °C

Procedure

A 100 mL round bottom flask was charged with tert-butyl 4-(5-bromo-3-cyanopyrazin-2-yl)piperazine-1-carboxylate (1.0 g, 2.7 mmol), thiophen-2-ylboronic acid (0.52 g, 4.1 mmol), Pd(PPh3)4 (0.31 g, 0.27 mmol), Cs2CO3 (1.4 g, 4.1 mmol), 1,4-dioxane (20 mL) and water (10 mL). The resulting mixture was heated at 100° C. overnight under N2 atmosphere. Work-up: the reaction mixture was poured into brine (80 mL) and extracted with EtOAc (30 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was further purified by flash column chromatography on silica gel with 30% EtOAc in petroleum ether, to afford 700 mg (70%) of the product.

Workup

extractionextracted with EtOAc (30 mL×3)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was further purified by flash column chromatography on silica gel with 30% EtOAc in petroleum ether

Sources & evidence

ORD record: ord-9c79e295aef449a08416e741730ef6cb
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569300B2

Reaction notes

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