Sodium Carbonate → 3-{3-[3-(2,2,2-Trifluoro-ethyl)-ureido]-phenyl}-imidazo[1,2-a]pyridine-7-carboxylic acid

HRID 536295Notes

Reaction equation

HRID 536295 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11](I)=[CH:12][N:13]=[C:7]2[CH:6]=1)=[O:4].CC1(C)C(C)(C)OB([C:23]2[CH:24]=[C:25]([NH:29][C:30]([NH:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[O:31])[CH:26]=[CH:27][CH:28]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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:35][C:34]([F:36])([F:37])[CH2:33][NH:32][C:30](=[O:31])[NH:29][C:25]1[CH:24]=[C:23]([C:11]2[N:8]3[CH:9]=[CH:10][C:5]([C:3]([OH:2])=[O:4])=[CH:6][C:7]3=[N:13][CH:12]=2)[CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 574976911-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-ureaHCID 57497695Methyl 3-iodoimidazo(1,2-a)pyridine-7-carboxylate

Product 1

HCID 252639003-{3-[3-(2,2,2-Trifluoro-ethyl)-ureido]-phenyl}-imidazo[1,2-a]pyridine-7-carboxylic acid

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-Iodo-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (3.02 g, 10 mmol) in DME (200 ml) was added 1-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (4.13 g, 12 mmol), 1M Na2CO3 (80 ml) [reaction degassed by bubbling N2 through] followed by tetrakis(triphenylphosphine)palladium(0) (0.58 g, 0.5 mmol). The mixture was heated at 80° C. overnight, then diluted with water and extracted with CH2Cl2. The aqueous layer was neutralised and loaded onto a reverse phase (C18) SPE (Solid Phase Extraction) cartridge. The cartridge was washed with H2O (2 column volumes) and eluted with MeOH (2 column volumes), the organic solvent removed in vacuo to afford the product as an off-white solid: 1H NMR (400 MHz, DMSO-d6): 12.31 (1H, s), 9.77 (1H, s), 8.85 (1H, d), 8.12 (1H, d), 8.04 (1H, s), 7.94 (1H, s), 7.84 (1H, s), 7.76 (1H, d), 7.39 (1H, t), 7.21 (1H, d), 4.05-3.90 (2H, m). MS: [M+H]+ 379.

Workup

  1. extractionextracted with CH2Cl2
  2. extractionloaded onto a reverse phase (C18) SPE (Solid Phase Extraction) cartridge
  3. washThe cartridge was washed with H2O (2 column volumes)
  4. washeluted with MeOH (2 column volumes)
  5. customthe organic solvent removed in vacuo

Sources & evidence

ORD record
ord-6f36559bdcab41d78826af955e1424d7
Source dataset
uspto-grants-2014_10
Patent number
US08859583B2

Reaction notes

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