Potassium Phosphate, Tribasic → HCID 45275782, compound

HRID 1622384Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:17]1([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[N:8]2[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 170 °C

Procedure

To a mixture of 1-(3-bromopyridin-4-yl)piperidine-4-carboxamide E36 (20 mg, 0.070 mmol), phenylboronic acid (17 mg, 0.14 mmol) and tetrakis (triphenylphosphine)palladium(0) (8 mg, 10 mol %) in toluene (1.5 mL) was added a 0 potassium phosphate (45 mg, 0.21 mmol). The mixture was heated at 170° C. in a microwave reactor for 45 min, then poured into a saturated solution of sodium hydrogen carbonate (25 mL). The mixture was extracted with EtOAc (2×20 mL) and the combined organic extracts were washed with brine (25 mL), dried (MgSO4) and the solvent was removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 95:5) to furnish the title compound as a white solid (5 mg, 25%), LC-MS (ESI, 3.5 min) Rt 1.28 min, m/z 282 (100%, [M+H]+), m/z (ESI) C17H20N3O requires 282.1601 found [M+H]+ 282.1597.

Workup

extractionThe mixture was extracted with EtOAc (2×20 mL)
washthe combined organic extracts were washed with brine (25 mL)
dry with materialdried (MgSO4)
customthe solvent was removed under reduced pressure
customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 95:5)

Sources & evidence

ORD record: ord-01e63c9c4bcb490594441c097f58f59d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778925B2

Reaction notes

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