Methanol → HCID 58399162, compound

HRID 475482Notes

Reaction equation

HRID 475482 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:25])[CH:12]2[CH2:24][N:16]3[C:17]4[C:22]([CH:23]=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:26](Cl)(=[O:30])[C:27](Cl)=[O:28].[CH3:32][OH:33].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:32][O:33][C:26](=[O:30])[C:27]([C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]2[CH2:24][CH:12]([N:11]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)(=[O:9])=[O:10])[CH3:25])[CH2:13][CH2:14][C:15]=12)=[O:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 58399171HCID 58399171, compound

Product 1

HCID 58399162HCID 58399162, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of (+/−) 4-fluoro-N-methyl-N-(6,7,8,9-tetrahydropyrido [1,2-α]indol-7-yl)benzenesulfonamide from Step 11 in CH2Cl2 (0.1 M) was added oxalyl chloride (2 equiv.) and the mixture was stirred for 1 h at 0° C. MeOH (20 equiv.) was added, the resulting mixture was stirred at rt for 1 h, and then poured into aqueous NaHCO3 and extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried with MgSO4 and concentrated under vacuum to afford the crude title compound (100%) as a yellow solid. The material was used as such in the next step.

Workup

  1. stirringthe resulting mixture was stirred at rt for 1 h
  2. extractionextracted with CH2Cl2 (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-94aebd39cda84139b27917e519ec97bd
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Reaction notes

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