Sodium Carbonate → 6-(Phenylethynyl)-5-(pyrimidin-5-yl)-[4,4'-bipyridin]-2-amine

HRID 923668Notes

Reaction equation

Br[C:2]1[C:3]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:4][C:5]([NH2:16])=[N:6][C:7]=1[C:8]#[C:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N:23]1[CH:28]=[C:27](B(O)O)[CH:26]=[N:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C(#N)C>[C:10]1([C:9]#[C:8][C:7]2[N:6]=[C:5]([NH2:16])[CH:4]=[C:3]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:2]=2[C:27]2[CH:28]=[N:23][CH:24]=[N:25][CH:26]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (30 mg, 26 μmol) is added to a mixture of 5-bromo-6-(2-phenylethynyl)-4-(pyridin-4-yl)pyridin-2-amine G8 (90 mg, 0.26 mmol), pyrimidine-5-boronic acid (48 mg, 0.39 mmol), sodium carbonate (aqueous solution, 2 mol/l, 0.39 ml, 0.78 mmol) and ACN (2.4 ml) under nitrogen atmosphere at RT and is stirred at 150° C. for 1 h. The mixture is concentrated in vacuo and the product purified by NP chromatography. Yield: 72 mg (80%). HPLC-MS: M+H=350; tR=1.11 min (METHOD—5).

Workup

concentrationThe mixture is concentrated in vacuo
customthe product purified by NP chromatography

Sources & evidence

ORD record: ord-56b248afaa56431194db859811ef09d7
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278978B2

Reaction notes

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