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[ CAS No. 6358-77-6 ] {[proInfo.proName]}

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Chemical Structure| 6358-77-6
Chemical Structure| 6358-77-6
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Product Details of [ 6358-77-6 ]

CAS No. :6358-77-6 MDL No. :MFCD04037882
Formula : C7H8BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :OPGNSNDTPPIYPG-UHFFFAOYSA-N
M.W :202.05 Pubchem ID :3585328
Synonyms :

Calculated chemistry of [ 6358-77-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.04
TPSA : 35.25 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) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.95
Log Po/w (XLOGP3) : 1.92
Log Po/w (WLOGP) : 2.05
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 1.78
Consensus Log Po/w : 1.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.68
Solubility : 0.422 mg/ml ; 0.00209 mol/l
Class : Soluble
Log S (Ali) : -2.28
Solubility : 1.05 mg/ml ; 0.0052 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.192 mg/ml ; 0.000948 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 6358-77-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6358-77-6 ]

* 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.

  • Upstream synthesis route of [ 6358-77-6 ]
  • Downstream synthetic route of [ 6358-77-6 ]

[ 6358-77-6 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 33696-00-3 ]
  • [ 6358-77-6 ]
YieldReaction ConditionsOperation in experiment
100% With ammonium chloride; zinc In ethanol at 20℃; for 2 h; [00169] Intermediate 1 1 A. 4-Bromo-l-methoxy-2-nitrobenzene: The mixture of 4- bromo- 1 -methoxy-2 -nitrobenzene (2.00 g, 8.62 mmol), zinc (5.64 g, 86.0 mmol), and ammonium chloride (4.61 g, 86.0 mmol) in ethanol (65 mL) was stirred together at room temperature for 2 h. The reaction was then diluted with EtOAc, filtered through CELITE®, and evaporated to give Intermediate 11A (1.74 g, 100percent) as a grayish-white solid. LCMS (ESI) m/z 202, 204 (M+H, M+2+H)+, RT = 0.70 min (Method J).
60%
Stage #1: With tin(II) chloride dihdyrate In ethanol at 70℃; for 2 h; Inert atmosphere
Stage #2: With water; sodium hydrogencarbonate In ethanolCooling with ice
A mixture of 11d (515 mg, 2.2 mmol) and SnCl2·2H2O (2.1 g, 10 mmol) in absolute ethanol (30 mL) was heated at 70 °C under argon for 2 h. The reaction mixture was allowed to cool to room temperature and then poured into ice. The pH was adjusted to 7–8 by addition of 5percent aqueous NaHCO3, and the mixture was extracted with EtOAc (2 × 30 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated. The residue was purified by column chromatography (cyclohexane/EtOAc/Et3N: 85/15/0.5) to give aniline 11e51 as a pink powder (260 mg, 60percent).
Reference: [1] Patent: WO2014/22343, 2014, A1, . Location in patent: Paragraph 00169
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1357 - 1366
[3] Journal fuer Praktische Chemie (Leipzig), 1935, vol. <2> 143, p. 18,24
[4] Gazzetta Chimica Italiana, 1932, vol. 62, p. 51,54
[5] Justus Liebigs Annalen der Chemie, 1883, vol. 217, p. 44
[6] Patent: US2004/122237, 2004, A1, . Location in patent: Page 371
[7] Patent: US2002/45615, 2002, A1,
[8] Patent: US2008/51395, 2008, A1, . Location in patent: Page/Page column 93; 124
[9] Patent: US2009/149456, 2009, A1, . Location in patent: Page/Page column 68
[10] Patent: US2015/18566, 2015, A1, . Location in patent: Paragraph 0632; 0633; 0634; 0635; 0636; 0637; 0638
  • 2
  • [ 104-92-7 ]
  • [ 6358-77-6 ]
Reference: [1] ACS Catalysis, 2016, vol. 6, # 12, p. 8162 - 8165
  • 3
  • [ 33696-00-3 ]
  • [ 7439-89-6 ]
  • [ 6358-77-6 ]
Reference: [1] Patent: US2003/187001, 2003, A1,
[2] Patent: US2003/187001, 2003, A1,
[3] Patent: US6303600, 2001, B1,
  • 4
  • [ 367521-06-0 ]
  • [ 6358-77-6 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 37, p. 9202 - 9203
  • 5
  • [ 33696-00-3 ]
  • [ 7646-78-8 ]
  • [ 6358-77-6 ]
Reference: [1] Patent: US2003/69239, 2003, A1,
  • 6
  • [ 7693-52-9 ]
  • [ 6358-77-6 ]
Reference: [1] Patent: US2015/18566, 2015, A1,
  • 7
  • [ 88301-40-0 ]
  • [ 6358-77-6 ]
Reference: [1] Gazzetta Chimica Italiana, 1932, vol. 62, p. 51,54
  • 8
  • [ 93-26-5 ]
  • [ 6358-77-6 ]
Reference: [1] Gazzetta Chimica Italiana, 1932, vol. 62, p. 51,54
  • 9
  • [ 7664-93-9 ]
  • [ 6358-77-6 ]
  • [ 82547-30-6 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 3523,3527
  • 10
  • [ 7647-01-0 ]
  • [ 7732-18-5 ]
  • [ 6358-77-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1883, vol. 217, p. 44
  • 11
  • [ 6358-77-6 ]
  • [ 73183-34-3 ]
  • [ 1000339-10-5 ]
YieldReaction ConditionsOperation in experiment
80% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 8 h; Inert atmosphere Synthesis of 2-methoxy-5-(4, 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 28.12
To potassium acetate (8.9 g, 90.83 mmol), bis-(pinacolato)-diboron (8.1 g, 31.86 mmol) and bis(diphenylphosphine) ferrocene dichloropalladium (II) (0.34 g, 0.48 mmol) was added an anhydrous solution of 5-bromo-2-methoxyaniline (3.22 g, 15.93 mmol) in DMSO (40 mL) under anhydrous conditions in an atmosphere of nitrogen.
The mixture was stirred at 80° C. for 8 h after which time the reaction was quenched with saturated NaCl aqueous solution (30 mL) and extracted with diethyl ether (3*20 mL).
The combined ether extracts were dried over magnesium sulphate, filtered and concentrated.
The crude product was purified by flash column chromatography (stationary phase; silica gel 230-400 mesh, mobile phase; 9:1 hexane/ethyl acetate).
All homogenous fractions were collected and reduced in volume to afford the product 28.12 as a brown syrup (3.18 g, 80percent).
νmax (DCM)/cm-1: 2926.38, 1599.02, 1431.11, 1356.01, 1221.39, 1142.48
1H NMR (CDCl3, 400 MHz) δH ppm: 1.35 (12H, s, 2*C(CH3)2), 3.89 (3H, s, OCH3), 6.15 (2H, br, NH2), 7.18 (1H, d, J 8.0 Hz, ArH), 7.25 (1H, d, J 2.5 Hz, ArH), 7.29 (1H, s, ArH).
13C NMR δc ppm: 24.5 (4*CH3), 55.1 (OCH3), 83.2 (2*C(CH3)2) 105.5 (ArCH), 113.7 (ArC), 120.6 (ArCH), 125.8 (ArCH), 135.0 (ArC), 149.7 (ArC).
30% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 48 h; Inert atmosphere 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (60a) (0303) 5-Bromo-2-methoxyaniline (500 mg, 2.48 mmol, 1.0 equiv), bis(pinacolato)diboron (691 mg, 2.72 mmol, 1.1 equiv), potassium acetate (730 mg, 7.44 mmol, 3.0 equiv) and Pd(dppf)Cl2 (54.4 mg, 74.4 μmol, 0.03 equiv) were dissolved under Argon atmosphere in 7 ml DMSO and the mixture was stirred at 80° C. for 48 h. Water was added and the aqueous layer was extracted with ethyl acetate three times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness. The raw product was purified by flash chromatography; yield: 30percent (184 mg). 1H NMR (300 MHz, acetone-d6): δ 7.11-7.02 (m, 2H), 6.81 (d, J=7.9 Hz, 1H), 3.84 (s, 3H), 1.29 (s, 12H).
Reference: [1] Patent: US2015/18566, 2015, A1, . Location in patent: Paragraph 0685; 0686; 0687; 0688; 0689
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3767 - 3793
[3] Patent: US2016/318895, 2016, A1, . Location in patent: Paragraph 0303
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