Potassium Carbonate → HCID 66705704, compound

HRID 1881522Notes

Reaction equation

HRID 1881522 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14]([CH2:19][C:20]2[N:21]([C:33]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH:22]=[C:23]([CH2:25][C:26]4([C:29]([F:32])([F:31])[F:30])[CH2:28][CH2:27]4)[N:24]=2)([OH:18])[CH2:13][CH2:12]3)O1.C(=O)([O-])[O-].[K+].[K+].Br[C:60]1[CH:65]=[CH:64][C:63]([F:66])=[CH:62][N:61]=1>CO.C1(C)C=CC=CC=1.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>[F:66][C:63]1[CH:64]=[CH:65][C:60]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14]([CH2:19][C:20]2[N:21]([C:33]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)[CH:22]=[C:23]([CH2:25][C:26]4([C:29]([F:31])([F:30])[F:32])[CH2:28][CH2:27]4)[N:24]=2)([OH:18])[CH2:13][CH2:12]3)=[N:61][CH:62]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27831712-Bromo-5-fluoropyridineHCID 66705658HCID 66705658, compound

Product 1

HCID 66705704HCID 66705704, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21867641Toluene methanolSolvent

Conditions

Temperature
90 °C

Procedure

Pd(PPh3)4 (264 mg, 0.23 mmol) was added to a degassed solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[(4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1-trityl-1H-imidazol-2-yl)methyl]indan-1-ol (1.61 g, 2.29 mmol), potassium carbonate (411 mg, 2.97 mmol), and 2-bromo-5-fluoropyridine (483 mg, 2.74 mmol) in methanol/toluene (5 mL/50 mL). The solution was stirred at 90° C. for 2 h. The solvent was removed in vacuo and the residue was redissolved in EtOAc (200 mL). The solution was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give a residue. The residue was purified by column chromatography eluting with 0-100% EtOAc/hexanes to give 5-(5-fluoropyridin-2-yl)-1-[(4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1-trityl-1H-imidazol-2-yl)methyl]indan-1-ol.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was redissolved in EtOAc (200 mL)
  3. washThe solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a residue
  8. customThe residue was purified by column chromatography
  9. washeluting with 0-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-58cbea31b5714ec4b406eb3379dfdec1
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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