2-Bromopyrimidine → HCID 44565636, compound

HRID 1913152Notes

Reaction equation

HRID 1913152 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([C:18]2[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=2)=[O:17])[CH2:12][CH2:11]1.Br[C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1.CC(C)([O-])C.[Na+]>CO.O1CCOCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:28]3[N:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:20][CH:19]=2)=[O:17])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 783452-BromopyrimidineHCID 23676156Sodium t-butoxideHCID 58494526HCID 58494526, compound

Product 1

HCID 44565636HCID 44565636, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (4-{[4-(1H-benzimidazol-2-yl)piperidin-1-yl]carbonyl}phenyl)boronic acid (0.349 g, 1.00 mmol), 2-bromopyrimidine (0.175 g, 1.10 mmol) and sodium tert-butoxide (0.106 g, 1.10 mmol) are suspended in a mixture of MeOH/1,4-dioxane (1 mL/2 mL). The suspension is purged with N2 before adding 1,1′-bis(diphenylphosphino)ferrocene-palladium (II) dichloride dichloromethane complex (41 mg, 5 mol %). The reaction is heated to 90° C. for 18 h. The mixture is diluted with EtOAc, washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue is triturated with MeCN and DCM to give 99 mg of [4-(1H-Benzimidazol-2-yl)piperidin-1-yl][4-(pyrimidin-2-yl)phenyl]methanone.

Workup

  1. customThe suspension is purged with N2
  2. additionbefore adding 1,1′-bis(diphenylphosphino)ferrocene-palladium (II) dichloride dichloromethane complex (41 mg, 5 mol %)
  3. additionThe mixture is diluted with EtOAc
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is triturated with MeCN and DCM

Sources & evidence

ORD record
ord-23c624f73d774b088d5ecea32d3230e3
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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