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Chemical Structure| 279256-09-6

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Product Details of [ 279256-09-6 ]

CAS No. :279256-09-6
Formula : C14H15NO3
M.W : 245.27
SMILES Code : O=C(N1C=CC2=C1C=CC(C=O)=C2)OC(C)(C)C
MDL No. :MFCD09029796
InChI Key :KDMYWOVAHWERQN-UHFFFAOYSA-N
Pubchem ID :11172622

Safety of [ 279256-09-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 279256-09-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 279256-09-6 ]

[ 279256-09-6 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 15893-47-7 ]
  • [ 279256-09-6 ]
  • [ 279255-90-2 ]
  • [ 879887-21-5 ]
  • [ 879887-65-7 ]
YieldReaction ConditionsOperation in experiment
11%; 55%; 12% With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 8h; D-Leucinamide (1.0 g, 6.0 mmol), 1-(t-butyloxycarbonyl)-5-formylindole (Example 1, 1.23 g, 5.0 mmol) and DCE (15 mL) were mixed at room temperature. Sodium triacetoxyborohydride (1.48 g, 7.0 mmol) was added in one portion with vigorous stirring. After 2 h, another portion (0.15 g, 0.7 mmol) was added and stirring was continued for an additional 6 h. The reaction mixture was diluted with a saturated NaHCO3 solution (10 mL). Three extractions with EtOAc, washing the combined organic layers with brine, drying over Na2SO4 and filtration provided a solution. Removal of solvent in vacuo afforded an oil. Column chromatography (DCM:MeOH:95:5) provided three fractions, after removal of solvent in vacuo: (1) 1-(t-Butyloxycarbonyl)-5-hydroxymethylindole (162 mg, 11% yield, Rf=0.5): 1H NMR (CDCl3, 300 MHz): 8.11 (d, 1H, J=8), 7.61 (d, 1H, J=2), 7.54 (s, 1H), 7.31 (dd, 1H, J=8,2), 6.55 (d, 1H, J=3), 4.75 (s, 2H), 1.69 (s, 9H); (2) 2R-bis-(1-t-butyloxycarbonylindol-5-ylmethyl)amino-4-methylpentanamide BMS594447 (382 mg, 12% yield, Rf=0.4): 1H NMR (CDCl3, 300 MHz): 8.1 (d, 2H, J=8), 7.61 (d, 2H, J=2), 7.52 (s, 2H), 7.31 (dd, 2H, J=8,2), 6.62 (m, 1H), 6.56 (d, 2H, J=4), 6.05 (br s, 1H), 3.85 (d, 2H, J=16), 3.66 (d, 2H, J=16), 3.35 (m, 1H), 1.69 (s, 18H), 0.96 (d, 3H, J=7), 0.87 (d, 3H, J=7); MS (ES+): 589.4 (C35H45N3O5) and (3) the title product (986 mg, 55% yield, Rf=0.3): 1H NMR (CDCl3, 300 MHz): 8.10 (d, 1H, J=8), 7.61 (d, 1H, J=2), 7.49 (d, 1H, J=1), 7.28-7.20 (m, 3H), 6.55 (d, 1H, J=4), 3.93 (d, 1H, J=16), 3.77 (d, 1H, J=16), 3.28-3.20 (m, 1H), 1.69 (s, 9H), 0.94 (d, 3H, J=7), 0.85 (d, 3H, J=7); MS (ES+): 360 (C20H30N3O3, M++H).
  • 2
  • [ 279255-90-2 ]
  • [ 279256-09-6 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; Step 3 To a solution of <strong>[279255-90-2]N-tert-butoxycarbonylindol-5-yl methanol</strong> (2.56 g, 10.35 mmol) in dry methylene chloride (60 mL) was added manganese oxide (9 g, 103.5 mmol). The reaction mixture was stirred for 3 h at room temperature and then heated at reflux. After 3 h, the heterogeneous slurry was filtered through Celite and concentrated to afford N-tert-butoxycarbonyl-5-formylindole (2.5 g).
With manganese(IV) oxide; In dichloromethane; at 40℃; for 25h; A solution of tert-butyl 5-([tert-butyl(dimethyl)silyl]oxy}methyl)-1H-indole-1- carboxylate (1-6, 13.0 g, 36.0 mmol, 1 equiv) and triethylamine trihydrofluoride (5.86 mL, 36.0 ralphamol, 1.00 equiv) in acetonitrile (150 mL) was stirred at 23 C for 20 h. The reaction mixture was concentrated, and the residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate (2 x 200 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (hexanes initially, grading to 60% EtOAc in hexanes) to provide the intermediate alcohol. A mixture of the alcohol and manganese (IV) oxide (6.25 g, 71.9 mmol, 2.00 equiv) in dichloromethane (200 mL) was heated at 40 C for 20 h. Additional manganese(IV) oxide (3.13 g, 36.0 mmol, 1.00 equiv) was added and heating was continued for 5 h. The solids were filtered and washed with dichloromethane (3 x 100 mL). The combined filtrate EPO <DP n="69"/>was concentrated to give tert-butyl 5-formyl-1H-indole-1-carboxylate (5-1) as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 10.07 (s, 1H), 8.29 (d, 1H, J = 8.8 Hz), 8.10 (d, 1H, J = 1.6 Hz), 7.86 (dd, 1H, J = 8.8, 1.8 Hz), 7.69 (d, 1H, J = 4.0 Hz), 6.70 (dd, 1H, J = 3.7, 0.6 Hz), 1.70 (s, 9H). LRMS m/z (M+H- CH3) 231.2 found, 231.1 required.
  • 3
  • [ 2840-44-0 ]
  • [ 279256-09-6 ]
  • C24H22FNO3 [ No CAS ]
  • 4
  • [ 279256-09-6 ]
  • [ 279255-90-2 ]
YieldReaction ConditionsOperation in experiment
83% With methanol; sodium tetrahydroborate; at 0 - 20℃; for 3h; To a solution of tert-butyl 5-formyl-1H-indo . g, 12.23 mmol) in methanol (30 mL) was added sodium tetrahydroborate (0.463 g, 12.23 mmol) at 0 C. The reaction mixture was stirred at 0 C for 3 hours then overnight at room temperature. The resulting solution was diluted with water (40 mL), then extracted with ethyl acetate (3 x 30 mL). The organic layers were combined, washed with aqueous sodium carbonate and brine, dried and concentrated under vacuum to afford tert-butyl 5-(hydroxymethyl)-1H-indole-1- carboxylate (2.5 g, 10.11 mmol, 83% yield) as a yellow oil. LCMS m/z = 270.3 [M+Na]+.
 

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