Hexane → HCID 86661827, compound

HRID 1042113Notes

Reaction equation

HRID 1042113 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]([NH2:32])=O)=[CH:17]3)=[CH:9][CH:8]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1.C(OCC)(=O)C.CCCCCC>O1CCCC1>[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:42])[NH2:32])=[CH:17]3)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 66725937HCID 66725937, compound

Product 1

HCID 86661827HCID 86661827, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-({6-[(2-methoxyethoxy)methyl]pyridin-3-yl}oxy)-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxamide (1.1 g) in tetrahydrofuran (20 mL) was added a Lawesson's reagent (1.1 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 (1.1 g, yield 96%) 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-340d242b6157400e879be19b483fa51e
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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