Potassium Carbonate → HCID 58056751, compound

HRID 561055Notes

Reaction equation

HRID 561055 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.[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=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 27343542-Fluorophenylboronic acidHCID 58056714HCID 58056714, compound

Product 1

HCID 58056751HCID 58056751, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

Following the procedures of example 14, (S)-benzyl-2-(8-bromoimidazo[1,2-a]pyridin-2-yl)pyrrolidine-1-carboxylate (0.2489 g, 0.62 mmol), 2-fluorophenyl boronic acid (0.1217 g, 0.87 mmol), potassium carbonate (0.1449 g, 1.05 mmol), and tetrakis(triphenylphosphine)-palladium(0) (0.0532 g, 0.05 mmol) produced the crude material which was adsorbed onto silica gel and purified by flash chromatography (4 g SiO2, 0-60% ethyl acetate in hexanes) to give (2S)-benzyl 2-(8-(2-fluorophenyl)imidazo[1,2-a]pyridin-2-yl)pyrrolidine-1-carboxylate (0.62 mmol, 100%).

Workup

  1. customproduced the crude material which
  2. custompurified by flash chromatography (4 g SiO2, 0-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2be02ce1ce81433aa56c0e1106d1e72c
Source dataset
uspto-grants-2011_11
Patent number
US08063218B2

Reaction notes

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