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[ CAS No. 1953-54-4 ] {[proInfo.proName]}

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Chemical Structure| 1953-54-4
Chemical Structure| 1953-54-4
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Product Details of [ 1953-54-4 ]

CAS No. :1953-54-4 MDL No. :
Formula : C8H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :LMIQERWZRIFWNZ-UHFFFAOYSA-N
M.W :133.15 Pubchem ID :16054
Synonyms :
5-Hydroxyindole

Calculated chemistry of [ 1953-54-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.32
TPSA : 36.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.16
Log Po/w (XLOGP3) : 1.03
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 0.91
Log Po/w (SILICOS-IT) : 2.1
Consensus Log Po/w : 1.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.98
Solubility : 1.39 mg/ml ; 0.0105 mol/l
Class : Very soluble
Log S (Ali) : -1.38
Solubility : 5.6 mg/ml ; 0.042 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.67
Solubility : 0.282 mg/ml ; 0.00212 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 1953-54-4 ]

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

Application In Synthesis of [ 1953-54-4 ]

* 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.

  • Upstream synthesis route of [ 1953-54-4 ]
  • Downstream synthetic route of [ 1953-54-4 ]

[ 1953-54-4 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 1953-54-4 ]
  • [ 56-45-1 ]
  • [ 4350-09-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 38, p. 11577 - 11581[2] Angew. Chem., 2016, vol. 128, p. 11749 - 11753,5
[3] Recueil des Travaux Chimiques des Pays-Bas, 1990, vol. 109, # 4, p. 287 - 297
[4] ChemCatChem, 2014, vol. 6, # 5, p. 1270 - 1276
[5] Chemistry - A European Journal, 2018, vol. 24, # 40, p. 10028 - 10031
  • 2
  • [ 1953-54-4 ]
  • [ 75-03-6 ]
  • [ 10501-17-4 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In acetone at 50℃; for 96 h; E1. 5-Ethoxy-indole; A mixture of commercially available 5-hydroxy-indole (18 g, 13.5 mmol), anhydrous K2CO3 (93.5 g, 5 equiv) and iodoethane (40.5 ml, 3.75 equiv) in acetone (180 ml_) is stirred at 50 0C under argon. When TLC (dichloromethane-methanol, 95:5) indicates the disappearance of 5-hydroxy-indole (4 days), the mixture is filtered, the solid is washed with acetone, then the filtrate is concentrated to give 17.67 g (90 percent) of the title compound, which is sufficiently pure to be used in the next step. M. p. 144-146 0C (from ethanol).
90% With potassium carbonate In acetone at 50℃; for 96 h; A mixture of commercially available 5-hydroxy-indole (18 g, 13.5 mmol), anhydrous K2CO3 (93.5 g, 5 equiv) and iodoethane (40.5 ml, 3.75 equiv) in acetone (180 ml_) is stirred at 50 0C under argon. When TLC (dichloromethane-methanol, 95:5) indicates the disappearance of 5-hydroxy- indole (4 days), the mixture is filtered, the solid is washed with acetone, then the filtrate is concentrated to give 17.67 g (90 percent) of the title compound, which is sufficiently pure to be used in the next step. M. p. 144-146 0C (from ethanol).
90% With potassium carbonate In acetone at 50℃; for 96 h; A mixture of commercially available 5-hydroxy-indole (18 g, 13.5 mmol), anhydrous K2CO3 (93.5 g, 5 equiv) and iodoethane (40.5 ml, 3.75 equiv) in acetone (180 mL) is stirred at 50 0C under argon. When TLC (dichloromethane-methanol, 95:5 v.v) indicates the disappearance of 5-hydroxy-indole (4 days), the mixture is filtered, the solid is washed with acetone, then the filtrate is concentrated to give 17.67 g (90 percent) of the title compound, which is sufficiently pure to be used in the next step. M. p. 144-1460C (from ethanol).
Reference: [1] Patent: WO2007/96395, 2007, A1, . Location in patent: Page/Page column 123
[2] Patent: WO2009/24190, 2009, A1, . Location in patent: Page/Page column 81
[3] Patent: WO2009/24613, 2009, A1, . Location in patent: Page/Page column 78
[4] Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2865 - 2874
  • 3
  • [ 67-56-1 ]
  • [ 1953-54-4 ]
  • [ 1125-40-2 ]
Reference: [1] ACS Catalysis, 2018, vol. 8, # 4, p. 3091 - 3103
  • 4
  • [ 153805-85-7 ]
  • [ 1953-54-4 ]
  • [ 1215-59-4 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen In tetrahydrofuran at 20℃; for 9 h; Following a procedure similar to Example 32, 4-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 5, and in the case where the reducing agent of the present invention was used, 5-benzyloxyindole was obtained in a higher yield and 5-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 4.
96% With hydrogen In tetrahydrofuran at 20℃; for 15 h; Following a procedure similar to Example 32, 4-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 5, and in the case where the reducing agent of the present invention was used, 5-benzyloxyindole was obtained in a higher yield and 5-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 4.
93% With hydrogen In tetrahydrofuran; water at 20℃; for 23 h; Following a procedure similar to Example 32, 4-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 5, and in the case where the reducing agent of the present invention was used, 5-benzyloxyindole was obtained in a higher yield and 5-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 4.
86% With hydrogen In tetrahydrofuran at 20℃; for 15 h; Following a procedure similar to Example 32, 4-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 5, and in the case where the reducing agent of the present invention was used, 5-benzyloxyindole was obtained in a higher yield and 5-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 4.

Reference: [1] Patent: EP1541582, 2005, A1, . Location in patent: Page/Page column 39
[2] Patent: EP1541582, 2005, A1, . Location in patent: Page/Page column 39
[3] Patent: EP1541582, 2005, A1, . Location in patent: Page/Page column 39
[4] Patent: EP1541582, 2005, A1, . Location in patent: Page/Page column 39
[5] Tetrahedron Letters, 2006, vol. 47, # 6, p. 969 - 972
[6] Tetrahedron Letters, 2006, vol. 47, # 6, p. 969 - 972
  • 5
  • [ 1953-54-4 ]
  • [ 100-39-0 ]
  • [ 1215-59-4 ]
YieldReaction ConditionsOperation in experiment
91% With 18-crown-6 ether; caesium carbonate In acetone at 20℃; 0.5 g (3.8 mmol) 5-hydroxyindole (1 ) were dissolved in 5 ml acetone and mixed with 535 μΙ (4.5 mmol) benzylbromide (BnBr), 2.45 g (7.5 mmol) Cs2C03 and 1.2 g (4.5 mmol) 18-crown-6 at room temperature (rt). After stirring for 2.5 to 17 h, preferably for 6 h, the mixture was diluted with water, smoothly acidified with 1 M HCI and extracted three times with CH2CI2. The combined organic layers were dried with Na2S04, filtered and evaporated. The crude product was purified by flash chromatography (Si02, cyclohexane - ethyl acetate 4:1 ) and yielded 762 mg (3.4 mmol, 91 percent) of a pale yellow solid. 1H-NMR (500 MHz, CDCl3): 8.11 (br, 1 H), 7.52 (d, J=7.5 Hz, 2 H), 7.41 (t, J=7.8 Hz, 2 H), 7.37-7.30 (m, 2 H), 7.22 (d, J=2.3 Hz, 1 H), 7.21 (t, J=2.8 Hz, 1 H), 6.98 (dd, J=8.8 Hz, J=2.4 Hz, 1 H), 6.51 (br, 1 H), 5.15 (s, 2 H).
91% With potassium carbonate In N,N-dimethyl-formamide for 24 h; Reflux Benzylbromide (2.0 mL, 16.8 mmol) and K2CO3 (3.1 g, 22.5 mmol) were added to a solution of 5-hydroxyindole 1 (2.0 g, 15.0 mmol) in DMF (10 mL) and the mixture was stirred and heated at reflux. After 24 h, the mixture was cooled to r.t. and the reaction was quenched with 10percent aq HCl. The mixture was extracted with EtOAc (3 50 mL), MgSO4. The solvent was removed and the residue was purified by silica gel column chromatography (EtOAc/hexane, 1:6) to give 2. Yield: 3 g (91percent); colorless solid; mp 97-100 °C (CHCl3). IR (CHCl3): 3483, 1626, 1581, 1477, 1452, 1281, 1153 cm-1. 1H NMR (500 MHz, CDCl3): δ = 8.03 (br. s, 1H), 7.52 (d, J = 7.5 Hz, 2 H), 7.43 (t, J = 7.5 Hz, 2 H), 7.36 (t, J = 7.5 Hz, 1H), 7.27 (d, J = 8.6 Hz, 1H), 7.24 (d, J = 2.3 Hz, 1H), 7.15 (t, J = 2.8 Hz, 1H), 6.99 (dd, J = 8.6, 2.3 Hz, 1H), 6.51 (t, J = 2.3 Hz, 1H), 5.15 (s, 2 H). 13C NMR (125 MHz, CDCl3): δ = 153.5, 137.8, 131.3, 128.7, 128.4, 127.9, 127.7, 125.1, 113.2, 111.9, 104.1, 102.5, 71.1. HRMS (EI): m/z [M+] calcd for C15H13NO: 223.0997; found: 223.1028.
88% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16 h; A mixture ofof5-hydroxyindole 1 (750 mg, 5.63 mmol), benzyl bromide (1.05 g, 6.19 mmol), K2C03 (2.30 g, 16.89 mmol) and DMF (10 mL), was stirred at RT for 16 h. The mixture was partitioned between water (100 mL) and EtOAc (50 mL). The organic layer was separated and the aq. layer re-extracted with additional EtOAc (50 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified (silica gel; eluting with 0-100percent EtOAc in hexanes), to afford compound 2 (1.12 g, 88percent) as a light yellow solid. LCMS Mass: 224.0 (M+1).
75% With tetrabutyl-ammonium chloride; sodium hydroxide In dichloromethane at 20℃; for 16 h; Compound 6 was prepared according to a previously described procedure32 with slight modifications. Tetrabutylammonium chloride (138.9 mg, 0.5 mmol) and benzylbromide (0.130 mL,1.1 mmol) were added to a solution of 5-hydroxy-1H-indole (5) (133.15, 1 mmol) in DCM (12 mL) and NaOH (20percent). The mixture was stirred for 16 h at room temperature. Then, it was poured into H2O (5 mL) and extracted with DCM (3 x 10 mL). The organic layer was dried over dry Na2SO4 and, after evaporation of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel using hexane/AcOEt 70:30 as eluent. Yield 75percent. Mp 96–98 °C. 1H NMR (CDCl3), (δ) 5.09 (s, 2H, CH2O), 3.46 (s, 1H, ArH, H-3), 6.91–7.47 (m, 10H, ArH), 8.02 (br s, 1H, NH). 13C NMR (CDCl3), 153.3, 137.6, 131.1, 128.5, 128.2, 127.7, 127.5,124.8, 113.0, 111.6, 103.9, 102.4, 70.8. Anal. C15H13NO (C, H, N). HPLC: 98.1percent. MS: m/z 224 (M+1).

Reference: [1] Patent: WO2014/125084, 2014, A1, . Location in patent: Page/Page column 28; 29
[2] Synthesis (Germany), 2017, vol. 49, # 18, p. 4141 - 4150
[3] Patent: WO2017/3862, 2017, A1, . Location in patent: Paragraph 00365
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 15, p. 4575 - 4580
[5] ChemMedChem, 2012, vol. 7, # 5, p. 910 - 919
[6] Patent: WO2005/30191, 2005, A1, . Location in patent: Page/Page column 41
[7] Patent: WO2005/30191, 2005, A1, . Location in patent: Page/Page column 41
  • 6
  • [ 1953-54-4 ]
  • [ 6953-22-6 ]
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 18, p. 4141 - 4150
  • 7
  • [ 1953-54-4 ]
  • [ 100-39-0 ]
  • [ 6953-22-6 ]
Reference: [1] Patent: WO2005/30191, 2005, A1,
  • 8
  • [ 1953-54-4 ]
  • [ 394-31-0 ]
Reference: [1] Synthetic Communications, 2010, vol. 40, # 23, p. 3480 - 3487
[2] Applied Organometallic Chemistry, 2011, vol. 25, # 1, p. 34 - 46
  • 9
  • [ 1953-54-4 ]
  • [ 68-12-2 ]
  • [ 3414-19-5 ]
Reference: [1] Phytochemistry, 2000, vol. 53, # 1, p. 59 - 69
[2] Farmaco, 1994, vol. 49, # 6, p. 443 - 448
[3] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 666 - 680
  • 10
  • [ 1953-54-4 ]
  • [ 172078-33-0 ]
YieldReaction ConditionsOperation in experiment
35%
Stage #1: at 20℃; for 1 h; Inert atmosphere
Stage #2: With sodium hydroxide In water
2,3-dihydro-1H-indol-5-ol
Under a nitrogen atmosphere 0.34 g sodium cyanoborohydride were added batchwise to 0.60 g (4.5 mmol) 5-hydroxyindole in 5.0 mL glacial acetic acid and the mixture was stirred for 60 min at RT.
Then the reaction mixture was poured onto a 4N aqueous sodium hydroxide solution and extracted with EtOAc.
The combined organic phases were washed several times with saturated sodium hydrogen carbonate solution, dried on sodium sulphate and evaporated down.
Yield: 265 mg (35percent of theoretical)
ESI-MS: m/z=136 (M+H)+
Rt (HPLC-MS): 0.38 min (method C)
32% at 25℃; for 12 h; Sodium cyanoborohydride (4.72 g, 75.1 mmol) was added portionwise to a solution of 5-hydroxy-1H-indole (4g, 30 mmol) in acetic acid (120 ml). The reaction solution was stirred at 25 °C for 12 hours, and then rotary evaporatedto remove the solvent, the residue was dissolved in ethyl acetate (200 ml), and washed with saturated sodium bicarbonate.The aqueous layer was extracted with ethyl acetate (3 x 150 ml). The organic layers were combined and washed withsaturated NaCl solution, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue waspurified by column chromatography (petroleum ether/ethyl acetate = 3: 1, Rf = 0.3) to give compound 24A (creamy whitesolid, 1.3 g, 32percent).1H NMR (400MHz, CHLOROFORM-d) = 6.69 (s, 1H), 6.59 - 6.49 (m, 2H), 3.55 (t, J=8.3 Hz, 2H), 3.01 (t, J=8.3 Hz, 2H),2.20 (s, 1H)
Reference: [1] Patent: US2011/21500, 2011, A1, . Location in patent: Page/Page column 46
[2] Patent: EP3293177, 2018, A1, . Location in patent: Paragraph 0217; 0218
[3] Patent: EP1154774, 2005, B1, . Location in patent: Page/Page column 118
  • 11
  • [ 75-30-9 ]
  • [ 1953-54-4 ]
  • [ 396091-50-2 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In acetonitrile at 20℃; for 48 h; [0374] To a solution of 5-hydroxyindole 23 (2.0 g, 0.015 mol) in 20 ml of acetonitrile, anhydrous potassium carbonate (4 grams, 0.028 mol) was added and stirred vigorously before isopropyl iodide (3 grams, 0. 018 mol) was added. The reaction was stirred for 2 days at room temperature and the solid was washed with acetonitrile. The filtrate was concentrated and purifed with flash-chromatography (80percent n-hexane/20percent ethyl acetate) to give the desired product 24 as a light-yellowish oil (1.72 g, 83percent ; M + 1 = 176. 1).
83% With potassium carbonate In acetonitrile Step 1-Synthesis of 5-Isopropoxy-indole 24
To a solution of 5-hydroxyindole 23 (2.0 g, 0.015 mol) in 20 ml of acetonitrile, anhydrous potassium carbonate (4 grams, 0.028 mol) was added and stirred vigorously before isopropyl iodide (3 grams, 0.018 mol) was added.
The reaction was stirred for 2 days at room temperature and the solid was washed with acetonitrile.
The filtrate was concentrated and purifed with flash-chromatography (80percent n-hexane/20percent ethyl acetate) to give the desired product 24 as a light-yellowish oil (1.72 g, 83percent; M+1=176.1).
Reference: [1] Patent: WO2005/9958, 2005, A1, . Location in patent: Page 102
[2] Patent: US2005/288354, 2005, A1,
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2865 - 2874
  • 12
  • [ 1953-54-4 ]
  • [ 75-26-3 ]
  • [ 396091-50-2 ]
Reference: [1] Patent: EP2108642, 2009, A1, . Location in patent: Page/Page column 92
  • 13
  • [ 1953-54-4 ]
  • [ 67-63-0 ]
  • [ 396091-50-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 14, p. 4085 - 4090
  • 14
  • [ 1953-54-4 ]
  • [ 269410-24-4 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 25, p. 6913 - 6917
  • 15
  • [ 1953-54-4 ]
  • [ 24424-99-5 ]
  • [ 434958-85-7 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With dmap In acetonitrile at 20℃; for 4 h;
Stage #2: With potassium carbonate In methanol at 20℃; for 4 h;
5-Hydroxyindole (3.49 g, 26.2 mmol) was dissolved in acetonitrile (35.0 mL), and the solution was added with di-tert-butyldicarbonate (18.1 mL, 78.6 mmol) and DMAP (294 mg, 2.62 mmol), followed by stirring at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (130 mL) and added with potassium carbonate (18.1 g, 131 mmol), followed by stirring at room temperature for 4 hours. The mixture was added with acetic acid (7.50 mL) to neutralize, and then added with water, followed by extracting with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate=2/1) to obtain 1-(tert-butoxycarbonyl)-5-hydroxyindole (5.74 g, 94percent). ESI-MS m/z: 234 [M+H]+; 1H-NMR (CDCl3)δ(ppm): 1.66 (s, 9H), 4.68 (s, 1H), 6.45 (d, J = 3.8 Hz, 1H), 6.83 (dd, J = 2.6, 8.9 Hz, 1H), 6.97 (d, J = 2.6 Hz, 1H), 7.56 (d, J = 3.8 Hz, 1H ), 7.98 (d, J = 8.9 Hz, 1H).
86%
Stage #1: With dmap In dichloromethane; acetonitrile at 20℃; for 1 h;
Stage #2: With potassium carbonate In methanol at 0 - 20℃; for 1.5 h;
To a solution of 5-hydroxyindole (2.02 g, 15.2 mmol, 1.0 eq) in MeCN (20 mL)was added di-tert-butyl dicarbonate (9.93 g, 45.5 mmol, 3.0 eq) and DMAP (186mg, 1.52 mmol, 10 molpercent). The reaction mixture was stirred at rt for 1 h then concentrated in vacuo, re-dissolved in CH2CI2 (20 mL) and washed with H20 (20 mL). The aqueous phase was extracted with CH2CI2 (20 mL) and the combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. Theresidue was then dissolved in MeOH (100 mL) and cooled to 0°C before the addition of potassium carbonate (10.5 g, 76 mmol, 5.0 eq) portionwise. The reaction was allowed to warm to rt and stirred for 1.5 h, then re-cooled to 0°C and quenched by the dropwise addition of acetic acid to neutralise the mixture. H20 (100 mL) was added and the resulting mixture was extracted with EtOAc (3x 100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. Purification twice by silica gel chromatography using hexane/EtOAc (1:0-6:1) then hexane/CH2CI2 (1:0-1:4) yielded Intermediate 49 as a white solid (3.05 g, 86percent).1H NMR (300MHz, DMSO-d5) oH. 9.18 (5, 1H), 7.82 (d, J=8.9 Hz, 1H), 7.55 (d,J=3.8 Hz, 1H), 6.92 (d, J=2.4 Hz, 1H), 6.77 (dd, J=8.9, 2.4 Hz, 1H), 6.54 (d, J=3.8 Hz, 1H), 1.56-1.64 (m, 9H).MS (ESj 256.1 (40percent, [M+Na]j.
71% With dmap In acetonitrile at 20℃; for 15 h; A solution of 5-hydroxyindole (III-1) (10 g, 75.1 mmol) in 100 mL of acetonitrile was added di-tert-butyl dicarbonate (49.2 g, 225.3 mmol) and DMAP (917 mg, 7.51 mmol) was stirred at room temperature for 15h; after completion of the reaction, the reactionmixture was concentrated under reduced pressure and 400mL of methanol was added to dissolve, then add K2CO.'s. 3(51.9 g, 375.5mmol), stirred at room temperature 4H;after completion of the reaction, the pH is adjusted with acetic acid , was added to neutrality H2O, and extracted the organic phase (ethyl acetate as the extractant), the solvent was removedagents, separation by column (petroleum ether: ethyl acetate = 3: 1) to give the product is the compound -2 ( 12.5 g, 71percent).
Reference: [1] Patent: EP2108642, 2009, A1, . Location in patent: Page/Page column 87
[2] Patent: WO2017/29521, 2017, A1, . Location in patent: Page/Page column 58
[3] Patent: CN107188900, 2017, A, . Location in patent: Paragraph 0093; 0094; 0095
  • 16
  • [ 1953-54-4 ]
  • [ 49761-82-2 ]
  • [ 434958-85-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 33, p. 8304 - 8308
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