Sodium Carbonate → HCID 59682038, compound

HRID 1394652Notes

Reaction equation

HRID 1394652 reaction equation
[CH:1]([C:4]1[C:5]([O:16][CH2:17]OC)=[C:6](B(O)O)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].[C:20](=O)([O-])[O-].[Na+].[Na+].[CH3:26][O:27][C:28]([C:30]1[CH:31]=[CH:32][C:33]2[N:34]([C:36](I)=[CH:37][N:38]=2)[CH:35]=1)=[O:29]>C1(C)C=CC=CC=1.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>[CH3:26][O:27][C:28]([C:30]1[CH:31]=[CH:32][C:33]2[N:34]([C:36]([C:6]3[CH:7]=[C:8]([CH:10]([CH3:11])[CH3:12])[CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]=3[O:16][CH2:17][CH3:20])=[CH:37][N:38]=2)[CH:35]=1)=[O:29]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10999969HCID 10999969, compoundHCID 16413170Methyl 3-iodoimidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 59682038HCID 59682038, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

3,5-Diisopropyl-2-methoxymethoxy-phenyl-boronic acid (455 mg, 1.83 mmol), followed by tetrakis(triphenylphosphine)palladium(0) (191 mg, 0.16 mmol), and 2M sodium carbonate solution (3.31 ml, 3.32 mmol) were added to a solution of 3-iodo-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (500 mg, 1.66 mmol) in toluene (10 mL). This reaction was then heated to 80° C. overnight, then cooled to ambient temperature and partitioned between brine (10 mL) and ethyl acetate (50 mL). The organic layer was dried over MgSO4 and evaporated to a residue. The residue was purified by silica gel chromatography (5% MeOH in dichlorometlane) to yield 3-(2-ethoxy-3,5-diisopropyl-phenyl)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester as a yellow solid (411 mg, 65%). 1H NMR (250 MHz, CDCl3): δ 8.71 (s, 1H), 7.70 (m, 1H), 7.62 (m, 1H), 7.41 (m 1H), 7.19 (d, 1H, J=1.2), 7.08 (d, 1H, J=1.2), 3.85 (s, 3H), 3.38 (m, 1H), 3.29 (q, 2H, J=6.8),2.90 (m, 1H), 1.28 (s, 3H), 1.26 (s, 6H), 1.24 (s, 3H), 0.75 (t, 3H, J=6.8). MS [EI+] 381 (M+H)+.

Workup

  1. temperaturecooled to ambient temperature
  2. custompartitioned between brine (10 mL) and ethyl acetate (50 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated to a residue
  5. customThe residue was purified by silica gel chromatography (5% MeOH in dichlorometlane)

Sources & evidence

ORD record
ord-b02312a48c0b49aeafa4b775b549ecfd
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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