Sodium Carbonate → HCID 58541903, compound

HRID 1966755Notes

Reaction equation

Br[C:2]1[CH:26]=[CH:25][C:5]2[N:6]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[O:19][C:18](=[O:20])[NH:17][N:16]=3)=[N:8][C:4]=2[CH:3]=1.[NH2:27][C:28]1[N:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[NH2:27][C:28]1[N:33]=[CH:32][C:31]([C:2]2[CH:26]=[CH:25][C:5]3[N:6]([C:21]([CH3:22])([CH3:24])[CH3:23])[C:7]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:15]4[O:19][C:18](=[O:20])[NH:17][N:16]=4)=[N:8][C:4]=3[CH:3]=2)=[CH:30][N:29]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a sealed vial is added 5-[2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-phenyl]-3H-[1,3,4]oxadiazol-2-one (40 mg, 0.097 mmol) in DMF (3 mL), followed by the addition of 2-aminopyrimidine-5-boronic acid pinacol ester (25 mg, 0.113 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (8 mg, 0.011 mmol) and 2M aq. Na2CO3 (0.2 ml, 0.4 mmol). The reaction mixture is heated under Argon at 100° C. for 6 hours. The residue is diluted with EtOAc (20 mL), washed with brine, dried under anhydrous Na2SO4, filtered and concentrated. The residue is purified by silica gel flash column chromatography with 0-10% 7M NH3 in MeOH/CH2Cl2 as the eluent to afford the title compound (4 mg, 10%) as a pale-white solid. LCMS (ESMS): m/z 428.87 (M++1).

Workup

washwashed with brine
customdried under anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue is purified by silica gel flash column chromatography with 0-10% 7M NH3 in MeOH/CH2Cl2 as the eluent

Sources & evidence

ORD record: ord-1232820426c64df4a645634989eca078
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420655B2

Reaction notes

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