Potassium Carbonate → HCID 58056715, compound

HRID 561051Notes

Reaction equation

HRID 561051 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([CH3:35])[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.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:26]1([CH3:35])[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:23]1[C:18]2[N:19]([CH:25]=[C:16]([C@@H:12]3[CH2:13][CH2:14][CH2:15][N:11]3[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[N:17]=2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 58056714HCID 58056714, compound

Product 1

HCID 58056715HCID 58056715, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Following procedures of example 14, (S)-benzyl-2-(8-bromoimidazo[1,2-a]pyridin-2-yl)pyrrolidine-1-carboxylate (0.250 g, 0.62 mmol), o-tolyl boronic acid (0.1101 g, 0.81 mmol), potassium carbonate (0.1292 g, 0.93 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.0360 g, 0.03 mmol) were reacted to give crude (2S)-benzyl 2-(8-o-tolylimidazo[1,2-a]pyridin-2-yl)pyrrolidine-1-carboxylate. The crude material was adsorbed onto silica gel and purified by flash chromatography (4 g SiO2, 0-70% ethyl acetate in hexanes) to give the final product (0.247 g, 0.60 mmol, 74%).

Workup

  1. customwere reacted
  2. customto give crude (2S)-benzyl 2-(8-o-tolylimidazo[1,2-a]pyridin-2-yl)pyrrolidine-1-carboxylate
  3. custompurified by flash chromatography (4 g SiO2, 0-70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f6146e9c08b247639bd864eb17ceff3d
Source dataset
uspto-grants-2011_11
Patent number
US08063218B2

Reaction notes

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