Sodium Carbonate → HCID 57906583, compound

HRID 420517Notes

Reaction equation

HRID 420517 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:10]2[CH:11]=[C:12](Br)[C:13]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:14][C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2].[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=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>[CH2:1]([O:3][C:4]([C:6]1[N:10]2[CH:11]=[C:12]([C:29]3[CH:28]=[CH:27][C:26]([Cl:25])=[CH:31][C:30]=3[Cl:32])[C:13]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:14][C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 57906588HCID 57906588, compound

Product 1

HCID 57906583HCID 57906583, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

In a sealed tube, a mixture of 6-bromo-7-(tert-butoxycarbonylamino-methyl)-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester (1.4 g, 3.52 mmol), 2,4-dichloro-benzeneboronic acid (1.01 g, 5.29 mmol), Pd(PPh3)4 (203 mg, 0.18 mmol) and Na2CO3 (2.0 M solution in water, 6.2 mL) in DME (20 mL) was heated at 150° C. for 17 min under microwave irradiation. The reaction mixture was cooled to RT, diluted in AcOEt (400 mL) and washed with a 2.0 M aqueous Na2CO3 solution (2×200 mL). The organic layer was dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→2:8) to yield the title compound (1.39 g, 2.81 mmol, 80%). MS: 464 [M+1]+; HPLC: AtRet=2.31; TLC: RF 0.47 (hexane/DCM/TBME 1:1:2).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with a 2.0 M aqueous Na2CO3 solution (2×200 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→2:8)

Sources & evidence

ORD record
ord-9c811ead7b3c4a5398ef540ab53b0e6c
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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