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Product Details of [ 51417-51-7 ]

CAS No. :51417-51-7 MDL No. :MFCD00799492
Formula : C8H6BrN Boiling Point : -
Linear Structure Formula :- InChI Key :RDSVSEFWZUWZHW-UHFFFAOYSA-N
M.W : 196.04 Pubchem ID :2757020
Synonyms :
Chemical Name :7-Bromoindole

Calculated chemistry of [ 51417-51-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.0
TPSA : 15.79 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) : -5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 2.74
Log Po/w (WLOGP) : 2.93
Log Po/w (MLOGP) : 2.31
Log Po/w (SILICOS-IT) : 3.25
Consensus Log Po/w : 2.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.45
Solubility : 0.0699 mg/ml ; 0.000357 mol/l
Class : Soluble
Log S (Ali) : -2.73
Solubility : 0.368 mg/ml ; 0.00188 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.14
Solubility : 0.0142 mg/ml ; 0.0000726 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.31

Safety of [ 51417-51-7 ]

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 [ 51417-51-7 ]

* 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 [ 51417-51-7 ]
  • Downstream synthetic route of [ 51417-51-7 ]

[ 51417-51-7 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 51417-51-7 ]
  • [ 557-21-1 ]
  • [ 96631-87-7 ]
YieldReaction ConditionsOperation in experiment
82% at 170℃; for 0.25 h; Microwave reactor 7-Cvano- lH-indole[0320] Pd(PPh3)4 (103 mg, 0.09 mmol) was added to 7-bromo-l //-indole (588 mg, 3 mmol) and Zn(CN)2 in degassed DMF (10 ml). The vial was capped and heated in the MW at 170 0C for 15 min. The reaction mixture was diluted with EtOAc and washed with water and brine, dried over sodium sulphate, filtered and concentrated in vacuo. The product <n="102"/>was purified by column chromatography (heptane 100percent to heptane/EtOAc 9:1) followed by recrystallization from heptane. Yield: 350 mg (82percent).[0321] 1H NMR (400 MHz5 CDCl3) δ 8.74 (br s, IH), 7.86 (d, IH, J = 8.0 Hz), 7.52 (d, IH, J= 7.6 Hz), 7.34 (t, IH, J= 2.6 Hz), 7.17 (t, IH5 J= 8.0 Hz), 6.65 (m, IH).
Reference: [1] Patent: WO2007/79239, 2007, A2, . Location in patent: Page/Page column 99-100
  • 2
  • [ 557-21-1 ]
  • [ 51417-51-7 ]
  • [ 96631-87-7 ]
Reference: [1] Patent: WO2009/153307, 2009, A1, . Location in patent: Page/Page column 31
[2] Patent: US2010/29729, 2010, A1, . Location in patent: Page/Page column 15
  • 3
  • [ 51417-51-7 ]
  • [ 96631-87-7 ]
YieldReaction ConditionsOperation in experiment
1.87 g at 200℃; for 2.5 h; Example 22
7-Cyano-1H-indole
Combine 7-bromoindole (4.72 g, 24.0 mmol) and copper cyanide (4.30 g, 48.1 mmol) in 1-methyl-2-pyrrolidine (40 mL).
Heat to 200 °C. After 2.5 hours, cool to room temperature, add water-ethyl acetate (200 mL, 1/1) to give a solid.
Filter through the celite, extract the filtrate with ethyl acetate, combine the organic layers, wash with brine, dry over Na2SO4, filter and evaporate in vacuo to give a residue.
Chromatograph the residue on silica gel eluting with hexanes : ethyl acetate (10 :1) to give (1.87 g) of the title compound as a yellow solid: 1H NMR (300 MHz, DMSO-d6)) 6.64-6.66 (m, 1H), 7.17 (t, 1H, J = 7.6 Hz), 7.51-7.53 (m, 1H), 7.60-7.62 (m, 1H), 7.94 (d, 1H, J = 8.0 H), 12.03 (br, 1H).
Reference: [1] Patent: EP1859798, 2015, B1, . Location in patent: Paragraph 0159
  • 4
  • [ 51417-51-7 ]
  • [ 201230-82-2 ]
  • [ 1670-83-3 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 1, p. 7 - 10
  • 5
  • [ 51417-51-7 ]
  • [ 5192-04-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1223 - 1226
[2] Patent: EP1813602, 2007, A1, . Location in patent: Page/Page column 6-7
  • 6
  • [ 51417-51-7 ]
  • [ 68-12-2 ]
  • [ 1074-88-0 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5106 - 5110
  • 7
  • [ 51417-51-7 ]
  • [ 69047-36-5 ]
Reference: [1] Journal of Organometallic Chemistry, 2011, vol. 696, # 5, p. 1072 - 1083
  • 8
  • [ 67-56-1 ]
  • [ 51417-51-7 ]
  • [ 201230-82-2 ]
  • [ 93247-78-0 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 10, p. 2167 - 2170
  • 9
  • [ 51417-51-7 ]
  • [ 79-22-1 ]
  • [ 93247-78-0 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 12, p. 2033 - 2039
  • 10
  • [ 51417-51-7 ]
  • [ 73183-34-3 ]
  • [ 642494-37-9 ]
YieldReaction ConditionsOperation in experiment
25 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 85℃; for 2 h; 7-bromoindole (20 g, 0.102mol) was dissolved in DMSO (100mL) in an 1 L single neck flask, and bis(pinacolato)diboron (39 g, 0.153 mol), [1,1’-bis(diphenylphosphino)ferrocene]dichloropalladium (Pd(dppf)Cl2, 4 g, 0.005 mol),and potassium acetate (15 g, 0.153 mol) were added. The system was heated to 85 °C to react for 2 h. Water was addedto quench the reaction. The mixture was extracted with ethyl acetate for 3 times, dried over sodium sulfate, concentrated,and subjected to column chromatography to obtain the product (25 g, 0.103 mol). 1H NMR (400 MHz, CDCl3): δ 9.29(s, 1H), 7.82 (d, J = 7.9 Hz, 1H), 7.70 (d, J = 7.0 Hz, 1H), 7.32-7.29 (m, 1H), 7.21-7.14 (m, 1H), 6.62-6.57 (m, 1H), 1.44(s, 12H). MS (ESI) (m/z): [M+H]+ 244.1.
Reference: [1] Synlett, 2003, # 8, p. 1204 - 1206
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 19, p. 3421 - 3427
[3] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[4] European Journal of Organic Chemistry, 2016, vol. 2016, # 27, p. 4621 - 4628
[5] Patent: JP2015/528445, 2015, A, . Location in patent: Paragraph 0047; 0065
[6] Patent: EP3345906, 2018, A1, . Location in patent: Paragraph 0332; 0333
  • 11
  • [ 51417-51-7 ]
  • [ 25015-63-8 ]
  • [ 642494-37-9 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 15, p. 5807 - 5810
[2] Patent: WO2006/10142, 2006, A2, . Location in patent: Page/Page column 83; 84
  • 12
  • [ 51417-51-7 ]
  • [ 642494-37-9 ]
Reference: [1] Heterocycles, 2010, vol. 80, # 2, p. 1267 - 1274
[2] Patent: US2015/318483, 2015, A1,
  • 13
  • [ 51417-51-7 ]
  • [ 852391-45-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 22, p. 5039 - 5044
  • 14
  • [ 51417-51-7 ]
  • [ 75-36-5 ]
  • [ 944086-09-3 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With diethylaluminium chloride In dichloromethane at 0℃; for 0.416667 h;
Stage #2: at 0℃; for 1 - 3 h;
Typical procedure 3 (See Scheme 2) (TP3):1 -(7-bromo-l -(3-chloroproρyO-l H-indol-3-yDethanone[0216] To a solution of 7-bromo-l //-indole (442 mg, 2.25 mmol) in dry CH2Cl2 (10 mL) at 0 0C was added Et2AlCl (3.4 mL, 1.0 M, 3.4 mmol) dropwise. The mixture was stirred at 0 0C for 25 min. A solution of AcCl (0.24 mL, 3.36 mmol) in CH2Cl2 (5 mL) was added dropwise and the mixture was stirred at 0 0C until TLC showed complete conversion of the indole (1-3 h). Saturated aqueous NaHCO3 (10 mL) was added slowly and the mixture was allowed to reach room temperature. The mixture was diluted with CH2Cb (60 mL) and the mixture was cautiously acidified to pH 4-5 with 2 M HCl (approx. 10 mL) to facilitate phase separation. The aqueous layer was extracted with CH2Cl2 (2x 10 mL) and the combined organic layers where washed with saturated aqueous NaHCψ3 and evaporated to dryness to give the acetylated compound (496 mg, 93percent). This acetyl ated crude product was dissolved in CH3CN (10 mL). To this solution was added Cs2CO3 (1.55 g, 4.76 mmol) and 1 - chloro-3-iodopropane (0.70 mL, 6.52 mmol) and the mixture was stirred at 50 0C overnight. The suspension was diluted with CH2Cl2 (70 mL), filtered and adsorbed onto celite. After purification by flash chromatography (heptanes - > heptanes: EtOAc 3:2) the title product was obtained (61 1 mg, 86percent over two steps. <n="78"/>[0217] 1H NMR (400 MHz, CDCl3) δ 8.41 (dd, J= 8.0, 1.1 Hz9 IH), 7.75 (s, IH), 7.44 (dd, J= 7.7, 1.1 Hz, IH), 7.12-7.08 (m, IH), 4.73 (t, J= 6.7 Hz, 2H), 3.50-3.47 (m, 2H), 2.50 (s, 3H), 2.39-2.33 (m, 2H).[0218] 13C NMR (100 MHz, CDCl3) δ 192.5, 137.7, 132.8, 129.7, 128.7, 123.7, 122.1, 1 16.5, 103.5, 45.8, 41.3, 34.1 , 27.5.
Reference: [1] Patent: WO2007/79239, 2007, A2, . Location in patent: Page/Page column 75-76
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4474 - 4489
[3] Chemical Communications, 2017, vol. 53, # 28, p. 3945 - 3948
[4] European Journal of Organic Chemistry, 2018, vol. 2018, # 12, p. 1426 - 1436
[5] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 702 - 707
  • 15
  • [ 51417-51-7 ]
  • [ 108-24-7 ]
  • [ 944086-09-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 4, p. 793 - 801
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