Ethyl isobutyrate → HCID 58052327, compound

HRID 2190209Notes

Reaction equation

HRID 2190209 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])[CH:14]([CH3:16])[CH3:15].[I:21][C:22]1[CH:23]=[C:24]2[C:40]([C:41]([NH:43][CH3:44])=[O:42])=[C:39]([C:45]3[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=3)[O:38][C:25]2=[N:26][C:27]=1[N:28]([CH2:33][CH2:34][CH2:35][CH:36]=[O:37])[S:29]([CH3:32])(=[O:31])=[O:30]>C1COCC1>[OH:37][CH:36]([CH2:35][CH2:34][CH2:33][N:28]([C:27]1[N:26]=[C:25]2[O:38][C:39]([C:45]3[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=3)=[C:40]([C:41](=[O:42])[NH:43][CH3:44])[C:24]2=[CH:23][C:22]=1[I:21])[S:29]([CH3:32])(=[O:31])=[O:30])[C:14]([CH3:16])([CH3:15])[C:13]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 7342Ethyl isobutyrateHCID 7912DiisopropylamineHCID 58052491HCID 58052491, compoundHCID 178418339Butyllithium

Product 1

HCID 58052327HCID 58052327, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamine (1.4 eq., 18 μl) in THF (0.5 ml) cooled at 0° C. was added n-BuLi (1.6 M in hexane, 1.2 eq., 68 μl). The resultant solution was stirred at 0° C. for 10 min and cooled to −78° C., and then a solution of ethyl isobutyrate (1 eq., 10.5 mg) in THF (0.5 ml) was added. After the reaction mixture was stirred at −78° C. for 1 h, a solution of 5-iodo-N-methyl-6-(N-(4-oxobutyl)methylsulfonamido)-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (1 eq., 50.0 mg) in THF (1 ml) was introduced. The reaction mixture was stirred at −78° C. for 1 h, quenched with saturated aqueous NH4Cl, and extracted with diethyl ether. The combined ethereal layers were washed with brine, dried over MgSO4, filtered, and concentrated to yield the crude title compound which was used in next step without purification.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 1 h
  2. customquenched with saturated aqueous NH4Cl
  3. extractionextracted with diethyl ether
  4. washThe combined ethereal layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-78e8b5130c1b40e585f5de01343cfe0f
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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