Sodium Carbonate → HCID 58547508, compound

HRID 1850339Notes

Reaction equation

HRID 1850339 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:15][CH:14]([C:16]2[C:21](Br)=[CH:20][N:19]=[C:18]([Cl:23])[N:17]=2)[CH2:13]1)=[O:11].C([O-])([O-])=O.[Na+].[Na+].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:15][CH:14]([C:16]2[C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:20][N:19]=[C:18]([Cl:23])[N:17]=2)[CH2:13]1)=[O:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58547470HCID 58547470, compound

Product 1

HCID 58547508HCID 58547508, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of (1H-benzoimidazol-2-yl)-[3-(5-bromo-2-chloro-pyrimidin-4-yl)-azetidin-1-yl]-methanone (206 mg, 0.53 mmol) in dioxane (15 mL) was treated with Na2CO3 (112 mg, 1.1 mmol dissolved 1 mL of H2O), followed by additional of phenylboronic acid (78 mg 0.64 mmol) and Pd(dppf)Cl2 (37 mg, 0.05 mmol). The resulting mixture was heated at refluxing overnight under N2 atmosphere. TLC showed that most of the staring materials were consumed completely. The solution was filtered, and the filter was concentrated. And the residue was purified by silica gel chromatography to give the product (102 mg, 0.28 mmol, yield: 53%). ESI-MS (M+1): 362 calc. for C21H16ClN5O 361.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat refluxing overnight under N2 atmosphere
  3. customwere consumed completely
  4. filtrationThe solution was filtered
  5. concentrationthe filter was concentrated
  6. customAnd the residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-22daed13dd2141de8b680ed9ca1630b9
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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