Potassium Carbonate → HCID 58285169, compound

HRID 1961516Notes

Reaction equation

[NH2:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[CH3:17][S:18]([C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=1)(=[O:20])=[O:19].C([O-])([O-])=O.[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C(O)(CC)(C)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]>[CH3:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([NH:1][C:2]2[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:12])([CH3:13])[CH3:14])[N:5]=[CH:4][C:3]=2[C:15]#[N:16])=[CH:23][CH:22]=1)(=[O:20])=[O:19]

Participants

Conditions

Temperature: 100 °C

Procedure

5-amino-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-4-carbonitrile (1.27 g, 5.33 mmol), 4-bromophenyl methyl sulfone (1.253 g, 5.33 mmol), Pd2 dba3 (0.244 g, 0.266 mmol), K2CO3 (0.810 g, 5.86 mmol) and X-Phos (0.635 g, 1.332 mmol) were taken up in tert-amyl alcohol (15 mL). The flask was evacuated and back-filled with N2 (×3) and the resulting mixture was stirred at 100° C. overnight. MeOH was added and the solvent removed in vacuo while loading onto silica. Purification of the residue by MPLC (12-100% EtOAc-hexanes) followed by MPLC (6-100% EtOAc-hexanes) gave 5-{[4-(methylsulfonyl)phenyl]amino}-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-4-carbonitrile as a hygroscopic yellow solid.

Workup

customThe flask was evacuated
additionback-filled with N2 (×3)
additionMeOH was added
customthe solvent removed in vacuo
customPurification of the residue by MPLC (12-100% EtOAc-hexanes)

Sources & evidence

ORD record: ord-ac01493d26bf4c6db87835a8edb91fcd
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415346B2

Reaction notes

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