1,2-Dimethoxyethane → HCID 67423639, compound

HRID 506957Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[N:15]=[C:14]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:13]=[N:12][CH:11]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].Cl[C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][N:27]=1.CC(C)([O-])C.[Na+].COCCOC>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:26]1([NH:1][C:2]2[CH:3]=[C:4]([C:10]3[N:15]=[C:14]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[CH:13]=[N:12][CH:11]=3)[CH:5]=[N:6][C:7]=2[O:8][CH3:9])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][N:27]=1

Participants

Conditions

Temperature: 90 °C

Procedure

tert-butyl 6-(5-amino-6-methoxypyridin-3-yl)pyrazin-2-ylmethylcarbamate (100 mg, 0.30 mmol, 1 eq.), 1-chloroisoquinoline (59 mg, 0.36 mmol, 1.2 eq.), Pd(OAc)2 (6.8 mg, 30.2 μmol, 0.1 eq.), Josiphos (16.7 mg, 30.2 μmol, 0.1 eq.) and sodium tert-butoxide (41 mg, 0.42 mmol, 1.4 eq.) were placed in a 2.5 mL V-bottomed Wheaton vial and dry DME (0.5 mL) was added. The resulting mixture was stirred at 90° C. overnight. The reaction mixture was allowed to cool to RT, diluted with DCM, silica (10 mL) added, concentrated under reduced pressure and purified by column chromatography (50% EtOAc in hexanes, dry loaded on silica, 100 mL silica) to give an ochre foam (76.6 mg, 56% Yield).

Workup

temperatureto cool to RT
additionadded
concentrationconcentrated under reduced pressure
custompurified by column chromatography (50% EtOAc in hexanes, dry loaded on silica, 100 mL silica)

Sources & evidence

ORD record: ord-828c0d52aac94e9385f8c464c1fbc73d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786130B2

Reaction notes

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