Pyridine → 2,2-Dimethyl-propionic acid 6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-8-yl-ester

HRID 2040463Notes

Reaction equation

HRID 2040463 reaction equation
[CH:1]1[C:6]2[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[CH2:16][S:17][C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:13][C:12]([OH:18])=[CH:11][CH:10]=4.N1C=CC=CC=1.[C:25](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])=[O:26]>C(Cl)Cl>[CH:1]1[C:6]2[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[CH2:16][S:17][C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:13][C:12]([O:18][C:25](=[O:26])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:11][CH:10]=4

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 444118686,11-Dihydrothiochromeno[4,3-b]indol-8-ol

Product 1

HCID 596761212,2-Dimethyl-propionic acid 6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-8-yl-ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-8-ol (1.01 g, 3.99 mmoL) in CH2Cl2 (5 mL) was treated with pyridine (0.387 mL, 4.788 mmoL) followed by PivCl (0.541 mL, 4.389 mmoL) at 0° C. The reaction mixture was slowly warmed to room temperature over 2 hours. The reaction mixture was then partitioned between CH2Cl2 and saturated NH4Cl. The aqueous phase was extracted two times with CH2Cl2. The organic layer from each extraction was combined, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material (the oil) was then purified by column chromatography (silica gel, hexanes:EtOAc 4:1 as eluent) to yield the title compound as a pale foam.

Workup

  1. customThe reaction mixture was then partitioned between CH2Cl2 and saturated NH4Cl
  2. extractionThe aqueous phase was extracted two times with CH2Cl2
  3. extractionThe organic layer from each extraction
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a brown oil
  9. customThe crude material (the oil) was then purified by column chromatography (silica gel, hexanes:EtOAc 4:1 as eluent)

Sources & evidence

ORD record
ord-3f3eb1f15a7d4b9bbbf497571cbd50b6
Source dataset
uspto-grants-2013_11
Patent number
US08580840B2

Reaction notes

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