Water → HCID 68668056, compound

HRID 216359Notes

Reaction equation

HRID 216359 reaction equation
[CH3:1][C:2]([CH3:51])([CH3:50])[CH2:3][C:4]1[N:5]=[C:6]([CH2:28][C:29]([C:35]2[CH:40]=[CH:39][C:38](B3OC(C)(C)C(C)(C)O3)=[CH:37][CH:36]=2)([OH:34])[C:30]([F:33])([F:32])[F:31])[N:7]([C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:59]1[CH:64]=[CH:63][C:62]([F:65])=[CH:61][N:60]=1.O>CN(C)C=O.O>[CH3:1][C:2]([CH3:51])([CH3:50])[CH2:3][C:4]1[N:5]=[C:6]([CH2:28][C:29]([C:35]2[CH:40]=[CH:39][C:38]([C:59]3[CH:64]=[CH:63][C:62]([F:65])=[CH:61][N:60]=3)=[CH:37][CH:36]=2)([OH:34])[C:30]([F:31])([F:32])[F:33])[N:7]([C:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27831712-Bromo-5-fluoropyridineHCID 68668175HCID 68668175, compound

Product 1

HCID 68668056HCID 68668056, compound

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (458 mg, 0.56 mmol) was added to a degassed, ambient temperature solution of 3-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-1,1,1-trifluoro-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propan-2-ol, sodium carbonate (2.4 g, 22.5 mmol) and 2-bromo-5-fluoropyridine (3.0 g, 16.8 mmol) in N,N-dimethylformamide/water (4:1) (150 mL). After stirring at 90° C. for 2 h, the reaction mixture was poured into water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-40% ethyl acetate/hexane afforded 3-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-1,1,1-trifluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]propan-2-ol.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5713c40235ae4f6aa29704252c370f1c
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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