Cesium carbonate → HCID 86725376, compound

HRID 1503819Notes

Reaction equation

[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[CH:14]=[C:13]([F:15])[C:12](Br)=[CH:11][C:10]=1[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:25]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[C:10]([F:17])=[CH:11][C:12]([N:28]2[CH2:27][CH2:26][N:25]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29]2)=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of the product of Example 15A (5.12 g, 13.2 mmol), tert-butyl piperazine-1-carboxylate (2.95 g, 15.8 mmol), palladium diacetate (149 mg, 0.66 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (616 mg, 0.99 mmol) and cesium carbonate (8.61 g, 26.4 mmol) in toluene (100 mL) was heated at 100° C. under nitrogen for 16 hours. After cooling, the mixture was filtered and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 5/1 petroleum ether/ethyl acetate to give the title compound. MS: 494 (M+H+).

Workup

temperatureAfter cooling
filtrationthe mixture was filtered
concentrationthe filtrate was concentrated
customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
washeluting with 5/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record: ord-1b6ad56bcce14ddcacc2c36e90f26e75
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212192B2

Reaction notes

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