Potassium Carbonate → N-Boc 4-(6-Cyano-2-oxo-2,3-dihydro-1H-indol-1-yl)-piperidine

HRID 2060048Notes

Reaction equation

[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:26])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][C:18]=2Br)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[K+].[K+].C1(B(O)O)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(C)(C)C>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]#[N:24])[CH:21]=3)[CH2:16][C:15]2=[O:26])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of N-Boc 4-{[(2-bromo-4-cyanophenyl)acetyl]amino}piperidine (D135, 100 mg, 0.189 mmol) in anhydrous degassed tert-butanol (2 mL) was treated with X-PHOS (10 mg, 0.021 mmol), potassium carbonate (70 mg, 0.506 mmol), palladium (II) acetate (2 mg, 8.91 μmol), and phenylboronic acid (2 mg, 0.016 mmol), then heated at 85° C. for 1 h then cooled and evaporated. Chromatography on silica (20 g), eluting with 10-50% ethyl acetate-isohexane, gave N-Boc-4-(6-cyano-2-oxo-2,3-dihydro-1H-indol-1-yl)-piperidine (40 mg, 0.117 mmol, 61.8% yield) as a colourless oil.

Workup

temperaturethen cooled
customevaporated
washChromatography on silica (20 g), eluting with 10-50% ethyl acetate-isohexane

Sources & evidence

ORD record: ord-fe9530bc40834335bb525bdda26bc73e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278328B2

Reaction notes

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