Acetic Anhydride → 4-Fluoro-3-(2-(3-(methylsulfinyl)-6-(morpholine-4-carbonyl)-1H-indol-1-yl)pyrimidin-5-yl)phenyl acetate

HRID 630512Notes

Reaction equation

HRID 630512 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[F:8][C:9]1[CH:14]=[CH:13]C(O)=C[C:10]=1[C:16]1[CH:17]=[N:18][C:19]([N:22]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:31]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[O:32])[CH:29]=3)[C:24]([S:39]([CH3:41])=[O:40])=[CH:23]2)=[N:20][CH:21]=1>N1C=CC=CC=1.O>[C:5]([O:4][C:1]1[CH:13]=[CH:14][C:9]([F:8])=[C:10]([C:16]2[CH:17]=[N:18][C:19]([N:22]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([C:31]([N:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)=[O:32])[CH:29]=4)[C:24]([S:39]([CH3:41])=[O:40])=[CH:23]3)=[N:20][CH:21]=2)[CH:2]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 118671888(1-(5-(2-Fluoro-5-hydroxyphenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(morpholino)methanone

Product 1

HCID 1186661794-Fluoro-3-(2-(3-(methylsulfinyl)-6-(morpholine-4-carbonyl)-1H-indol-1-yl)pyrimidin-5-yl)phenyl acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.18 mL, 1.9 mmol) was added at 0° C. to 264a) (0.45 g, 0.94 mmol) in pyridine (2.0 mL) and the resulting solution was stirred at room temperature for 3 h. The reaction mixture was diluted with cold water and extracted with dichloromethane/methanol (9:1; 3×30 mL). The organic layers were washed with saturated sodium hydrogen carbonate solution (2×20 mL) and brine (20 mL), dried over sodium sulfate and evaporated. The remnant was purified by flash column chromatography [silica; dichloromethane with 1.5% methanol]. Yield: 0.09 g (38% of theory)

Workup

  1. extractionextracted with dichloromethane/methanol (9:1; 3×30 mL)
  2. washThe organic layers were washed with saturated sodium hydrogen carbonate solution (2×20 mL) and brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe remnant was purified by flash column chromatography [silica; dichloromethane with 1.5% methanol]

Sources & evidence

ORD record
ord-f218a312769e4a6d8c62c31cd292b86e
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

Loading…