Potassium Phosphate, Tribasic → HCID 66597796, compound

HRID 422498Notes

Reaction equation

HRID 422498 reaction equation
Br[C:2]1[C:3]2[N:4]([CH:8]=[C:9]([CH2:11][CH2:12][C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][F:22])[N:16]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.CCOC(C)=O.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:22][CH2:21][C:17]1[N:16]=[C:15]([C:14]#[C:13][CH2:12][CH2:11][C:9]2[N:10]=[C:3]3[C:2]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:7][CH:6]=[CH:5][N:4]3[CH:8]=2)[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 66597800HCID 66597800, compound2×

Product 1

HCID 66597796HCID 66597796, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-bromo-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-Imidazo[1,2-a]pyridine (compound 171(C), 301 mg, 0.84 mmol) and phenylboronic acid (50 mg, 1.3 mmol) in degazed DME (4.2 mL) was added 1.32 mL of a solution of K3PO4 2M (degazed before use). After stirring at room temperature for 5 min under N2, Pd(PPh3)4 (190 mg, 0.17 mmol) was added in one portion. The resulting mixture was heated at 80° C. for 4 h. The mixture was cooled down to room temperature and diluted in AcOEt. The organic layer was washed twice with saturated NaCl, dried over magnesium sulfate, filtered and concentrated. The crude product was purified over silicagel chromatography (repacked 25 g silicagel column, Cyclohexane/AcOEt 60/40 as eluent) to afford 137 mg of 2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-8-phenyl-imidazo[1,2-a]pyridine-(Yield: 46%) as a yellow oil.

Workup

  1. temperatureThe resulting mixture was heated at 80° C. for 4 h
  2. temperatureThe mixture was cooled down to room temperature
  3. washThe organic layer was washed twice with saturated NaCl
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified over silicagel chromatography (repacked 25 g silicagel column, Cyclohexane/AcOEt 60/40 as eluent)

Sources & evidence

ORD record
ord-b14835f0b44c434cae95a6c68ce0188c
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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