Cesium carbonate → 3-[(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)amino]pyridine-2-carbonitrile

HRID 2109953Notes

Reaction equation

Br[C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:10]([C:14]1[CH:18]=[C:17]([NH2:19])[N:16]([CH3:20])[N:15]=1)([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:10]([C:14]1[CH:18]=[C:17]([NH:19][C:2]2[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=2)[N:16]([CH3:20])[N:15]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-bromopyridine-2-carbonitrile (150 mg, 0.98 mmol), 3-tert-butyl-1-methyl-1H-pyrazol-5-amine (179 mg, 0.98 mmol), cesium carbonate (638 mg, 1.96 mmol), BINAP (98 mg, 0.16 mmol) and Pd2(dba)3 (90 mg, 0.10 mmol) was taken in anhydrous toluene (2 mL) and heated to 80° C. for 24 h under nitrogen atmosphere. The reaction mixture was cooled to rt, diluted with ethyl acetate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography using EtOAc/Hex (1:9 to 1:4, v/v) as the eluent. The product was obtained as a yellow oil (145 mg, 58%). ES-MS m/z 256.1 (MH+); HPLC RT (min) 2.37.

Workup

temperatureThe reaction mixture was cooled to rt
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-db151f4822a9469ca071079bb5e0e5e3
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517878B2

Reaction notes

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