Methanol → HCID 58081048, compound

HRID 1042164Notes

Reaction equation

HRID 1042164 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[N:11]=[CH:10][C:9]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[C:20]([O:22][CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[CH:21]=2)[NH:18][C:17]([C:29](=[S:31])[NH2:30])=[CH:16]3)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[C:32]([O:37][CH2:38][CH3:39])(=[O:36])[C:33]#[C:34][CH3:35].C(P(CCCC)CCCC)CCC.CO>O1CCCC1.C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[CH2:38]([O:37][C:32](=[O:36])[CH2:33][CH:34]1[S:31][C:29]([C:17]2[NH:18][C:19]3[C:15]([CH:16]=2)=[CH:14][C:13]([O:12][C:9]2[CH:10]=[N:11][C:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:7][CH:8]=2)=[CH:21][C:20]=3[O:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:30][CH2:35]1)[CH3:39]

Participants

9

Reactant 4

HCID 887MethanolHCID 13831TributylphosphineHCID 78043Ethyl 2-butynoateHCID 86661830HCID 86661830, compound

Product 1

HCID 58081048HCID 58081048, compoundYield 61.5%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-({6-[(methylsulfonyl)methyl]pyridin-3-yl}oxy)-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carbothioamide (2.25 g) in tetrahydrofuran (10 mL) and toluene (15 mL) were added ethyl 2-butynoate (1.37 g) and tri-n-butylphosphine (0.99 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 silica gel column chromatography (methanol:ethyl acetate:hexane=0:0:100 to 5:95:0, volume ratio) to give the title compound (1.72 g, yield 61%) as a yellow amorphous solid.

Workup

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

Sources & evidence

ORD record
ord-4870a286d5664c4da41c135c451e4401
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

Loading…