Sodium Carbonate → HCID 67225872, compound

HRID 1966764Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[N:20]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]3[CH:25]=[CH:26][C:27](Br)=[CH:28][C:18]=3[N:17]=2)[N:6]=1)=[O:4].CC1(C)C(C)(C)OB([C:38]2[CH:39]=[N:40][C:41]([NH2:44])=[N:42][CH:43]=2)O1.[C:46]([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][NH:2][C:3]([C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:46])=[CH:12][C:11]=2[C:16]2[N:20]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]3[CH:25]=[CH:26][C:27]([C:38]4[CH:39]=[N:40][C:41]([NH2:44])=[N:42][CH:43]=4)=[CH:28][C:18]=3[N:17]=2)[N:6]=1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-[2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-phenyl]-[1,2,4]oxadiazole-5-carboxylic acid methylamide (150 mg, 0.32 mmol) in DMF (2 mL) in a sealed vessel are added 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine (85 mg, 0.38 mmol), 2 M Na2CO3 solution (0.48 mL, 0.96 mmol) and PdCl2(PPh3)2 (11 mg, 0.02 mmol) at room temperature. The solution is heated to 80° C. for 2 hours. The reaction mixture is cooled to room temperature and filtered through diatomaceous earth and concentrated in vacuo. Purification via flash chromatography (10 g silica gel, 2-3.5% MeOH/CH2Cl2) affords the title compound (18.4 mg, 12%). LCMS (ESMS): m/z 469.30 (M++1)

Workup

temperatureThe reaction mixture is cooled to room temperature
filtrationfiltered through diatomaceous earth
concentrationconcentrated in vacuo
customPurification via flash chromatography (10 g silica gel, 2-3.5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-894919f5609a49999e7d62ec5b261aeb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420655B2

Reaction notes

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