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[ CAS No. 24985-85-1 ]

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Chemical Structure| 24985-85-1
Chemical Structure| 24985-85-1
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CAS No. :24985-85-1 MDL No. :MFCD00015458
Formula : C11H11NO3 Boiling Point : 410.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :205.21 g/mol Pubchem ID :90677
Synonyms :

Safety of [ 24985-85-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24985-85-1 ]

  • Upstream synthesis route of [ 24985-85-1 ]
  • Downstream synthetic route of [ 24985-85-1 ]

[ 24985-85-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 37033-95-7 ]
  • [ 24985-85-1 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen In ethanol for 20 h; A solution of 5-benzyloxyindole-2-carboxylic acid ethyl ester (10 g, 34 mmol) in ethanol (250 mL) was treated with 10percent Pd/C and hydrogenated under atmospheric pressure (double-walled balloon) for 20 h. The reaction mixture was diluted with EtOAc and filtered through Celite. Evaporation of the filtrate in vacuo gave the title compound as a tan solid (7 g, 99percent). 1H NMR (400 MHz, CDCl3) δ 8.86 (br s, 1H), 7.29 (d, J=8.80 Hz, 1H), 7.11 (s, 1H), 7.06 (s, 1H), 6.94 (d, J=8.70 Hz, 1H), 4.83 (br s, 1H), 4.42 (q, J=7.09 Hz, 2H), 1.41 (t, J=7.08 Hz, 3H).
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 1, p. 5 - 8
[2] Patent: US6670388, 2003, B1, . Location in patent: Page column 6
[3] Patent: US6469046, 2002, B1,
[4] Patent: US6608059, 2003, B1,
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 24, p. 10455 - 10463
[6] Journal of Medicinal Chemistry, 1987, vol. 30, # 6, p. 1029 - 1035
[7] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5834 - 5856
  • 2
  • [ 4792-58-9 ]
  • [ 24985-85-1 ]
YieldReaction ConditionsOperation in experiment
82% With boron tribromide In dichloromethane Step 2:
Ethyl 5-hydroxyindole-2-carboxylate.
A mixture of 5.34 g (24.3 mmol) of ethyl 5-methoxyindole-2-carboxylate was stirred in 40 ml of CH2Cl2 at 0° C. under Ar while 40.0 ml of 1.0 M BBr3 in CH2Cl2 was added slowly over a period of 0.5 hour.
The reaction mixture was stirred for 2 hours more at which time the reaction was complete.
The mixture was extracted with EtOAc, washed with brine and water, dried (MgSO4), filtered, and concentrated.
Flash column chromatography (30percent EtOAc/hexane) yielded a pale-yellow solid (4.07 g, 82percent): m.p. 142-144° C.; Rf 0.18 (20percent EtOAc/hexane); 1H NMR (400 MHz, CDCl3) δ1.41 (t, J=7.2 Hz, 3, CH3), 4.40 (q, J=7.2 Hz, 2, CH2), 4.70 (s, 1, OH), 6.93 (dd, J=8.4, 1.6 Hz, 1, ArH), 7.06 (d, J=2.8 Hz, 1, ArH), 7.10 (s, 1, ArH), 7.29 (d, J=9.2 Hz, 1, ArH), 8.79 ppm (s, 1, NH).
48% With boron tribromide In diethyl ether; dichloromethane i
Ethyl 5-hydroxyindole-2-carboxylate
Boron tribromide (64.58 g) was added dropwise to a stirred solution of ethyl 5-methoxyindole-2-carboxylate (20 g) in dichloromethane (1000 ml) at -78° C. under an atmosphere of argon.
The reaction was allowed to warm to room temperature and stirred for a further 2 hours.
The reaction was poured into ice/saturated aqueous sodium hydrogen carbonate solution with stirring and extracted with ethyl acetate.
Combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution, water, aqueous saturated sodium chloride solution and dried.
The solution was concentrated in vacuo and the residue was purified by column chromatography using 0-60percent diethyl ether: iso-hexane as eluent to yield product as a white solid (9.02 g, 48percent). NMR(CD3SOCD3): δ 1.31 (t, 3H), 4.29 (q, 2H), 6.79 (dd, 1H), 6.90 (dd, 1H), 7.22 (d, 1H), 8.84 (s, 1H), 11.52 (brs, 1H); m/z 206 (MH+).
48% With boron tribromide In diethyl ether; dichloromethane i)
Ethyl 5-hydroxyindole-2-carboxylate
Boron tribromide (64.58 g) was added dropwise to a stirred solution of ethyl 5-methoxyindole-2-carboxylate (20 g) in dichloromethane (1000 ml) at -78° C. under an atmosphere of argon.
The reaction was allowed to warm to room temperature and stirred for a further 2 hours.
The reaction was poured into ice/s aqueous sodium hydrogen carbonate solution with stirring and extracted with ethyl acetate.
Combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution, water, aqueous saturated sodium chloride solution and dried.
The solution was concentrated in vacuo and the residue was purified by column chromatography using 0-60percent diethyl ether, iso-hexane as eluent to yield product as a white solid (9.02 g, 48percent). NMR: 1.31 (t, 3H), 4.29 (q, 2H), 6.79 (dd, 1H), 6.90 (dd, 1H), 7.22 (d, 1H), 8.84 (s, 1H), 11.52 (brs, 1H; m/z 206 M+H+).
48% With boron tribromide In dichloromethane at -78 - 20℃; for 2 h; [00211] Boron tribromide (64.58 g) was added dropwise to a stirred solution of ethyl 5-methoxyindole-2-carboxylate (20 g) in dichloromethane (1000 ml) at -78° C. under an atmosphere of argon. The reaction was allowed to warm to room temperature and stirred for a further 2 hours. The reaction was poured into ice/saturated aqueous sodium hydrogen carbonate solution with stirring and extracted with ethyl acetate. Combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution, water, aqueous saturated sodium chloride solution and dried. The solution was concentrated in vacuo and the residue was purified by column chromatography using 0-60percent diethyl ether: iso-hexane as eluent to yield product as a white solid (9.02 g, 48percent). NMR: δ 1.31) (t, 3H), 4.29 (q, 2H), 6.79 (dd, 1H), 6.90 (dd. 1H), 7.22 (d, 1H), 8.84 (s, 1H), 11.52 (brs, 1H); m/z 206 (M+H+).

Reference: [1] Patent: US2003/176506, 2003, A1,
[2] Patent: US2003/144339, 2003, A1,
[3] Patent: US6984657, 2006, B1,
[4] Patent: US6737435, 2004, B1, . Location in patent: Page/Page column 18-19
  • 3
  • [ 21598-06-1 ]
  • [ 64-17-5 ]
  • [ 24985-85-1 ]
YieldReaction ConditionsOperation in experiment
92% for 4 h; Reflux; Inert atmosphere 5-Hydroxyindole-2-carboxylicacid 30 (1.53 g, 8.6 mmol) was boiled under reflux in EtOH (100 mL)saturated with HCl under N2 for 4 h. The evaporation residue, EtOAc,was washed (water, brine). Drying, evaporation and chromatography (CH2Cl2→ CH2Cl2 / EtOAc 4:1) gave 31 (1.64 g, 92percent) as awhite solid: mp 152-154°C (lit.3 146-148°C); IR νmax 3316,3209, 1696 cm-1; 1H NMR ((CD3)2SO) d 1.38 (3 H, t, J = 7.1 Hz, Me), 4.37 (2 H, q, J= 7.1 Hz, CH2), 6.86 (1 H, dd, J= 8.8, 2.4 Hz, 6-H), 6.97 (1 H, d, J= 2.3 Hz, 4-H), 7.00 (1 H, dd, J =2.1, 0.8 Hz, 3-H), 7.32 (1 H, d, J =8.8 Hz, 7-H), 8.93 (1 H, s, OH), 11.60 (1 H, s, NH). 13C NMR ((CD3)2SO)d 14.29 (Me), 60.17 (CH2), 104.43(4-C), 106.66 (3-C), 113.07 (7-C), 116.15 (6-C), 127.36 (2-C or 3a-C), 127.44 (3a-C or 2-C),132.21 (7a-C), 151.34 (5-C), 161.30 (C=O)
86% for 12 h; Reflux To the solution of compound 1 (5 g, 0.028 mol) in EtOH (250 mL) was added H2SO4(0.5 mL). The mixture was heated to reflux for 12 h. After cooled to RT, the reaction mixture was concentrated and dissolved in DCM (100 mL). The DCM layer was washed with sat.NaHCO3, dried over Na2SO4, concentrated to give compound 2 (5.0 g, 86percent yield) as white solid.
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3481 - 3489
[2] Patent: JP2015/214548, 2015, A, . Location in patent: Paragraph 1400; 1401
[3] European Journal of Medicinal Chemistry, 2010, vol. 45, # 2, p. 752 - 759
  • 4
  • [ 617-35-6 ]
  • [ 123-30-8 ]
  • [ 24985-85-1 ]
Reference: [1] Journal of Organic Chemistry, 2018,
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