5-Bromopyrimidine → HCID 21876226, compound

HRID 724189Notes

Reaction equation

[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[C:6]2[CH:17]=[CH:18][C:19](B3OC(C)(C)C(C)(C)O3)=[CH:20][C:5]=2[N:4]=1)[CH3:2].Br[C:31]1[CH:32]=[N:33][CH:34]=[N:35][CH:36]=1.C([O-])(O)=O.[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:3]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][OH:16])=[CH:12][CH:13]=2)[C:6]2[CH:17]=[CH:18][C:19]([C:31]3[CH:32]=[N:33][CH:34]=[N:35][CH:36]=3)=[CH:20][C:5]=2[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-{4-[2-ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-1-yl]phenyl}ethanol (step 1, 100 mg, 0.26 mmol) and 5-bromopyrimidine (45 mg, 0.28 mmol) in 1,2-dimethoxyethane (3.5 ml) was added sat. NaHCO3 aq. (1.2 ml) and Pd(PPh3)4 (60 mg, 0.05 mmol). This mixture was stirred at 70° C. for 17 h. The reaction mixture was diluted with water and extracted with CH2Cl2 (3×10 ml). The organic layer was dried (MgSO4) and concentrated to give light brown oil. This mixture was purified by SiO2 preparative TLC (CH2Cl2/methanol=10/1) to afford 45 mg (50%) of the title compound.

Workup

extractionextracted with CH2Cl2 (3×10 ml)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated
customto give light brown oil
customThis mixture was purified by SiO2 preparative TLC (CH2Cl2/methanol=10/1)

Sources & evidence

ORD record: ord-5d81b841020e4fcda1c430c913fa2abc
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141580B2

Reaction notes

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