Ethyl Acetate → HCID 58081013, compound

HRID 1042160Notes

Reaction equation

HRID 1042160 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[N:12]=[CH:11][C:10]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[C:21]([O:23][CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:22]=2)[NH:19][C:18]([C:30](=[S:32])[NH2:31])=[CH:17]3)=[CH:9][CH:8]=1.[C:33]([O:38][CH2:39][CH3:40])(=[O:37])[C:34]#[C:35][CH3:36].C(P(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1.C1(C)C=CC=CC=1.CCCCCC>[CH2:39]([O:38][C:33](=[O:37])[CH2:34][CH:35]1[S:32][C:30]([C:18]2[NH:19][C:20]3[C:16]([CH:17]=2)=[CH:15][C:14]([O:13][C:10]2[CH:11]=[N:12][C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:8][CH:9]=2)=[CH:22][C:21]=3[O:23][CH:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)=[N:31][CH2:36]1)[CH3:40]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 13831TributylphosphineHCID 78043Ethyl 2-butynoateHCID 86661827HCID 86661827, compound

Product 1

HCID 58081013HCID 58081013, compoundYield 32.5%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-({6-[(2-methoxyethoxy)methyl]pyridin-3-yl}oxy)-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carbothioamide (1.1 g) in tetrahydrofuran (10 mL) and toluene (15 mL) were added ethyl 2-butynoate (0.67 g) and tri-n-butylphosphine (0.49 g), and the mixture was stirred at 90° C. for 1 hr. The reaction mixture was cooled, and concentrated under reduced pressure. The obtained crude product was subjected to basic silica gel column chromatography (ethyl acetate:hexane=0:100 to 50:50, volume ratio) to give the title compound (445 mg, yield 32%) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained crude product

Sources & evidence

ORD record
ord-e575024723ad41c98f82c5aad6ec78dd
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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