Hexane → HCID 86661830, compound

HRID 1042120Notes

Reaction equation

HRID 1042120 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]([NH2:31])=O)=[CH:16]3)=[CH:8][CH:7]=1)(=[O:4])=[O:3].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1.C(OCC)(=O)C.CCCCCC>O1CCCC1>[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[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[CH:21]=2)[NH:18][C:17]([C:29](=[S:41])[NH2:31])=[CH:16]3)=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 66726152HCID 66726152, compound

Product 1

HCID 86661830HCID 86661830, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-({6-[(methylsulfonyl)methyl]pyridin-3-yl}oxy)-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxamide (3.0 g) in tetrahydrofuran (20 mL) was added a Lawesson's reagent (3.0 g), and the mixture was stirred with heating under reflux for 1 hr. The reaction mixture was cooled, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=0:100 to 100:0, volume ratio) to give the title compound (2.26 g, yield 73%) as a yellow amorphous solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained crude product

Sources & evidence

ORD record
ord-79bca232da43404090336872dd022c06
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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