Potassium Carbonate → HCID 58056729, compound

HRID 561054Notes

Reaction equation

HRID 561054 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[N:17]=[C:18]2[C:23](Br)=[CH:22][CH:21]=[CH:20][N:19]2[CH:25]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1(B(O)O)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>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>[C:34]1([C:23]2[C:18]3[N:19]([CH:25]=[C:16]([C@@H:12]4[CH2:13][CH2:14][CH2:15][N:11]4[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])[N:17]=3)[CH:20]=[CH:21][CH:22]=2)[C:35]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 58056714HCID 58056714, compound

Product 1

HCID 58056729HCID 58056729, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Following the procedures of example 14, (S)-benzyl-2-(8-bromoimidazo[1,2-a]pyridin-2-yl)pyrrolidine-1-carboxylate (0.250 g, 0.62 mmol), 1-napthyl boronic acid (0.1405 g, 0.82 mmol), potassium carbonate (0.1340 g, 0.97 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.0430 g, 0.04 mmol) produced the crude material which was adsorbed onto silica gel and purified by flash chromatography (4 g SiO2, 0-50% ethyl acetate in hexanes) to give (2S)-benzyl 2-(8-(naphthalen-1-yl)imidazo[1,2-a]pyridin-2-yl)pyrrolidine-1-carboxylate (0.183 g, 0.41 mmol, 66%).

Workup

  1. customproduced the crude material which
  2. custompurified by flash chromatography (4 g SiO2, 0-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8046c37626a94227a5ec5193397fbf79
Source dataset
uspto-grants-2011_11
Patent number
US08063218B2

Reaction notes

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