Methanol → HCID 56941124, compound

HRID 1843988Notes

Reaction equation

HRID 1843988 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:19][C:20]1[CH:28]=[CH:27][C:26]2[N:25](S(C3C=CC=CC=3)(=O)=O)[C:24]3[CH2:38][CH2:39][N:40]([C:43]4[CH:44]=[N:45][CH:46]=[CH:47][C:48]=4[CH3:49])[C:41](=[O:42])[C:23]=3[C:22]=2[CH:21]=1.CO>C1COCC1.C(Cl)Cl>[F:19][C:20]1[CH:28]=[CH:27][C:26]2[NH:25][C:24]3[CH2:38][CH2:39][N:40]([C:43]4[CH:44]=[N:45][CH:46]=[CH:47][C:48]=4[CH3:49])[C:41](=[O:42])[C:23]=3[C:22]=2[CH:21]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 2724141Tetrabutylammonium FluorideHCID 66807275HCID 66807275, compound

Product 1

HCID 56941124HCID 56941124, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1M TBAF (0.3 mL, 0.274 mmol) was added to a solution of 8-fluoro-2-(4-methylpyridin-3-yl)-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (I-60b: 60 mg, 0.137 mmol) in THF (5 mL) at 0° C. and the resulting reaction mass was refluxed for 1 hour. The reaction was monitored by TLC (5% methanol in DCM). The reaction mass was concentrated under reduced pressure and the crude residue was partitioned between water and ethyl acetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated to afford the crude product. Purification by preparative HPLC afforded 20 mg of the product (52% yield).

Workup

  1. customthe resulting reaction mass
  2. temperaturewas refluxed for 1 hour
  3. concentrationThe reaction mass was concentrated under reduced pressure
  4. customthe crude residue was partitioned between water and ethyl acetate
  5. washThe organic layer was washed with water, brine solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto afford the crude product
  9. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-f7809b704b8748a0a0052e3047c6caf7
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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