[ CAS No. 6855-64-7 ] {[proInfo.proName]}

Name: 6855-64-7|2-Phenyl-1H-indol-5-amine|97%
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Quality Control of [ 6855-64-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 6855-64-7 ]

CAS No. :	6855-64-7	MDL No. :	MFCD17012057
Formula :	C₁₄H₁₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BQXQPVNUVFCTJS-UHFFFAOYSA-N
M.W :	208.26	Pubchem ID :	9837182
Synonyms :

Calculated chemistry of [ 6855-64-7 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	15
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	2.0
Molar Refractivity :	68.14
TPSA :	41.81 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.83
Log Po/w (XLOGP3) :	3.03
Log Po/w (WLOGP) :	3.43
Log Po/w (MLOGP) :	2.4
Log Po/w (SILICOS-IT) :	3.39
Consensus Log Po/w :	2.82

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.67
Solubility :	0.0447 mg/ml ; 0.000215 mol/l
Class :	Soluble
Log S (Ali) :	-3.57
Solubility :	0.0556 mg/ml ; 0.000267 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.45
Solubility :	0.000744 mg/ml ; 0.00000357 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.87

Safety of [ 6855-64-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6855-64-7 ]

* 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 [ 6855-64-7 ]
Downstream synthetic route of [ 6855-64-7 ]

[ 6855-64-7 ] Synthesis Path-Upstream 1~9

1
[ 4993-87-7 ]
[ 6855-64-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With hydrogen In methanol at 20℃;	To a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 2-phenyl-1H-indol-5-amine (1.6 g, 77percent). ¹H NMR (400 MHz, CDCl₃) δ 7.76 (d, J=7.6 Hz, 2H), 7.39 (t, J=7.6 Hz, 2H), 7.24 (t, J=7.6 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 6.64 (d, J=1.6 Hz, 1H), 6.60 (d, J=1.2 Hz, 1H), 6.48 (dd, J=2.0, 8.4 Hz, 1H), 4.48 (brs, 2H); MS (ESI) m/e (M+H⁺) 209.0.
77%	With hydrogen In methanol at 20℃; Inert atmosphere	To a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 2-phenyl-1H-indol-5-amine (1.6 g, 77percent). ¹H NMR (400 MHz, CDCl₃) δ 7.76 (d, J=7.6 Hz, 2H), 7.39 (t, J=7.6 Hz, 2H), 7.24 (t, J=7.6 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 6.64 (d, J=1.6 Hz, 1H), 6.60 (d, J=1.2 Hz, 1H), 6.48 (dd, J=2.0, 8.4 Hz, 1H), 4.48 (brs, 2H); MS (ESI) m/e (M+H⁺) 209.0.

Reference： [1] Tetrahedron Letters, 2002, vol. 43, # 43, p. 7699 - 7702
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 4085 - 4093
[3] Patent: US2007/244159, 2007, A1, . Location in patent: Page/Page column 120
[4] Patent: US2011/98311, 2011, A1,
[5] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 1672
[6] Organic and Biomolecular Chemistry, 2012, vol. 10, # 44, p. 8835 - 8847

2
[ 108-86-1 ]
[ 1227410-09-4 ]
[ 6855-64-7 ]

Reference： [1] Patent: US2005/197331, 2005, A1, . Location in patent: Page/Page column 16

3
[ 6293-83-0 ]
[ 536-74-3 ]
[ 6855-64-7 ]

Reference： [1] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4423 - 4426
[2] Organic and Biomolecular Chemistry, 2012, vol. 10, # 44, p. 8835 - 8847

4
[ 500992-02-9 ]
[ 6855-64-7 ]

Reference： [1] Tetrahedron Letters, 2002, vol. 43, # 43, p. 7699 - 7702

5
[ 120830-42-4 ]
[ 6855-64-7 ]

Reference： [1] Journal of the American Chemical Society, 1958, vol. 80, p. 3291
[2] Bulletin de la Societe Chimique de France, 1958, p. 23,29

6
[ 857555-71-6 ]
[ 6855-64-7 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1958, p. 23,29
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 5375,5376

7
[ 16720-35-7 ]
[ 6855-64-7 ]

Reference： [1] Journal of the American Chemical Society, 1958, vol. 80, p. 3291

8
[ 165280-21-7 ]
[ 6855-64-7 ]

Reference： [1] Patent: US2015/231142, 2015, A1,

9
[ 536-74-3 ]
[ 6855-64-7 ]

Reference： [1] Patent: US2015/231142, 2015, A1,

[ 6855-64-7 ] Synthesis Path-Downstream 1~35

1
[ 6855-64-7 ]
[ 108-24-7 ]
[ 4771-09-9 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 5375,5376

2
[ 120830-42-4 ]
[ 6855-64-7 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 3291

3
[ 857555-71-6 ]
[ 6855-64-7 ]

Reference： [1]Bulletin de la Societe Chimique de France,1958,p. 23,29

4
[ 6855-64-7 ]
[ 120-46-7 ]
1,3-diphenyl-3-(2-phenyl-5-indolylamino)-2-propen-1-one [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 1299 - 1303
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1520 - 1524

5
[ 6855-64-7 ]
[ 123-54-6 ]
4-(2-phenyl-5-indolylamino)-3-penten-2-one [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 1299 - 1303
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1520 - 1524

Yield	Reaction Conditions	Operation in experiment
83%		5a) 2-phenyl-5-amino-1H-indole Prepared in a manner similar to that of Example 4a. Yield: (83percent); Rf (2/1 hexane/ethyl acetate): 0.30; m.p.. 220.2-220.5°C.Elem. anal. C14H12N2; theory C:80.74 H:5.81 N:13.45; found C:80.55 H:5.76 N:13.35; IR (KBr): 3416, 3036, 1622, 1585 cm-1.
		(b) A mixture of 7.86 g. 5-nitro-2-phenylindole, 100 ml. absolute ethanol and 10 g. (wet weight) Grace No. 28 Raney nickel (previously washed with water and with absolute ethanol) is hydrogenated at ca. 3 atmospheres pressure and ca. 27° in a Parr apparatus. Hydrogen absorption ceases in ca. 3 hours and the reaction mixture, after dilution with ca. 300 ml. methylene chloride is filtered thru a Celite bed. The insolubles are washed with methylene chloride and with boiling ethanol. Removal of solvent from the combined organic solutions yields 6.51 g. 5-amino-2-phenylindole, m.p. 227°-229° (softens 217°), Noland et al., J. Org. Chem., 31, 65 (1966), prepared this amine similarly and reported m.p. 234°-235°. Addition of excess isopropanolic hydrogen chloride to a solution of 6.42 g.

7
[ 4993-87-7 ]
[ 6855-64-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With hydrogen;nickel; In methanol; at 20℃; under 760.051 Torr;	To a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 2-phenyl-1H-indol-5-amine (1.6 g, 77percent). 1H NMR (400 MHz, CDCl3) delta 7.76 (d, J=7.6 Hz, 2H), 7.39 (t, J=7.6 Hz, 2H), 7.24 (t, J=7.6 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 6.64 (d, J=1.6 Hz, 1H), 6.60 (d, J=1.2 Hz, 1H), 6.48 (dd, J=2.0, 8.4 Hz, 1H), 4.48 (brs, 2H); MS (ESI) m/e (M+H+) 209.0.
77%	In methanol;	2-Phenyl-1H-indol-5-amineTo a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere.The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight.The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 2-phenyl-1H-indol-5-amine (1.6 g, 77percent).1H NMR (400 MHz, CDCl3) delta 7.76 (d, J=7.6 Hz, 2H), 7.39 (t, J=7.6 Hz, 2H), 7.24 (t, J=7.6 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 6.64 (d, J=1.6 Hz, 1H), 6.60 (d, J=1.2 Hz, 1H), 6.48 (dd, J=2.0, 8.4 Hz, 1H), 4.48 (brs, 2H); MS (ESI) m/e (M+H+) 209.0.
77%	With hydrogen; In methanol; at 20℃; under 760.051 Torr;Inert atmosphere;	To a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 2-phenyl-1H-indol-5-amine (1.6 g, 77percent). 1H NMR (400 MHz, CDCl3) delta 7.76 (d, J=7.6 Hz, 2H), 7.39 (t, J=7.6 Hz, 2H), 7.24 (t, J=7.6 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 6.64 (d, J=1.6 Hz, 1H), 6.60 (d, J=1.2 Hz, 1H), 6.48 (dd, J=2.0, 8.4 Hz, 1H), 4.48 (brs, 2H); MS (ESI) m/e (M+H+) 209.0.

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 7699 - 7702
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 4085 - 4093
[3]Patent: US2007/244159,2007,A1 .Location in patent: Page/Page column 120
[4]Patent: US2011/98311,2011,A1
[5]Patent: US2015/231142,2015,A1 .Location in patent: Paragraph 1672
[6]Organic and Biomolecular Chemistry,2012,vol. 10,p. 8835 - 8847

8
[ 6855-64-7 ]
[ 777-44-6 ]
<i>N</i>-(2-phenyl-1<i>H</i>-indol-5-yl)-3-trifluoromethyl-benzenesulfonamide [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 7699 - 7702

9
[ 6855-64-7 ]
[ 141-97-9 ]
(Z)-3-[(2-phenyl-1H-5-indolyl)amino]crotonic acid ethyl ester [ No CAS ]
(E)-3-[(2-phenyl-1H-5-indolyl)amino]crotonic acid ethyl ester [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2003,vol. 39,p. 1188 - 1196

10
[ 6855-64-7 ]
[ 372-31-6 ]
[ 748799-38-4 ]
(Z)-4,4,4-trifluoro-3-[(2-phenyl-1H-5-indolyl)amino]crotonic acid ethyl ester [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2003,vol. 39,p. 1188 - 1196

11
[ 6855-64-7 ]
[ 87-13-8 ]
2-[(2-phenyl-1H-5-indolyl)aminomethylene]malonic acid diethyl ester [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2003,vol. 39,p. 1188 - 1196

12
[ 6855-64-7 ]
[ 108-56-5 ]
diethyl (5-amino-2-phenyl-1H-indolyl)fumarate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2007,vol. 43,p. 67 - 75

13
[ 6855-64-7 ]
7-ethoxycarbonyl-2-phenyl-6,9-dihydro-3H-pyrrolo[3,2-f]quinolin-9-one [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2007,vol. 43,p. 67 - 75

14
[ 6855-64-7 ]
2-phenyl-8-trifluoromethyl-5,6-dihydro-1H-pyrrolo[2,3-g]quinol-6-one [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2003,vol. 39,p. 1188 - 1196

15
[ 6855-64-7 ]
2-phenyl-7-trifluoromethyl-6,9-dihydro-3H-pyrrolo[3,2-f]quinol-9-one [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2003,vol. 39,p. 1188 - 1196

16
[ 6855-64-7 ]
1,5-dimethyl-2-phenyl-8-trifluoromethyl-5,6-dihydro-1H-pyrrolo[2,3-g]quinol-6-one [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2003,vol. 39,p. 1188 - 1196

17
[ 6855-64-7 ]
9-hydroxy-2-phenyl-3H-pyrrolo[3,2-f]quinoline-8-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2003,vol. 39,p. 1188 - 1196

18
[ 500992-02-9 ]
[ 6855-64-7 ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 7699 - 7702

19
[ 6855-64-7 ]
2-phenyl-7,9-dimethylpyrrolo<3,2-f>quinoline [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 1299 - 1303
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1520 - 1524

20
[ 6855-64-7 ]
2-phenyl-4,6-dimethylpyrrolo<2,3-g>quinoline [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 1299 - 1303
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1520 - 1524

21
[ 6855-64-7 ]
2,7,9-triphenylpyrrolo<3,2-f>quinoline [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 1299 - 1303
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1520 - 1524

22
[ 6855-64-7 ]
2,6,8-triphenylpyrrolo<2,3-g>quinoline [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 1299 - 1303
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1520 - 1524

23
[ 16720-35-7 ]
[ 6855-64-7 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 3291

24
C₂₉H₃₆N₂O₆ [ No CAS ]
[ 6855-64-7 ]

Yield	Reaction Conditions	Operation in experiment
		Bromobenzene (0.157 ml, 0.0014 mol) and dichlorobis(triphenylphosphine)palladium (II) (51.3 mg, 0.073 mmol) are added to 2-boronic acid 1-N-BOC-5-(N',N'-bisBOC)aminoindole (0.69 g, 0.0014 mol) in THF (10 ml). The mixture is refluxed for 24 hours, 4N HCl (4 ml) are added and the resulting mixture is heated at 80°C for 10 hours. The resulting mixture is basified with 4M NaOH (pH = 10) and extracted with ethyl acetate. The organic phases are combined, washed with water, dried, filtered and concentrated. The solid obtained is recrystallized from isopropyl ether. Rf (2/1 hexane/ethyl acetate): 0.30; m.p. 220.2-220.5°C. Elem. anal. C19H12N2 theory C:80.74 H:5.81 N:13.45; found C:80.55 H:5. 76 N:13.35; 1H-NMR (d6-DMSO) 11.0 (s, 1H, exch. D2O); 7.8 (dd, J = 8.6Hz, 1.5Hz, 1H); 7.6-7.20 (m, 4H); 7.05 (d, J = 8.6Hz, 1H); 6.8-6.3 (m, 3H); 4.5 (bs, 2H, exch. D2O).

Reference： [1]Patent: EP1571142,2005,A1 .Location in patent: Page/Page column 22

25
[ 108-86-1 ]
[ 1227410-09-4 ]
[ 6855-64-7 ]

Yield	Reaction Conditions	Operation in experiment
		Bromobenzene (0.157 ml, 0.0014 mol) and dichlorobis(triphenylphosphine)palladium (II) (51.3 mg, 0.073 mmol) are added to 2-boronic acid 1-N-BOC-5-(N',N'-bisBOC)aminoindole (0.69 g, 0.0014 mol) in THF (10 ml). The mixture is refluxed for 24 hours, 4N HCl (4 ml) are added and the resulting mixture is heated at 80° C. for 10 hours. The resulting mixture is basified with 4M NaOH (pH=10) and extracted with ethyl acetate. The organic phases are combined, washed with water, dried, filtered and concentrated. The solid obtained is recrystallized from isopropyl ether. Rf (2/1 hexane/ethyl acetate): 0.30; m.p.: 220.2-220.5° C. Elem. anal. C14H12N2 theory C, 80.74; H, 5.81; N, 13.45. found C, 80.55; H, 5.76; N, 13.35. 1H-NMR (d6-DMSO) 11.0 (s, 1H, exch. D2O); 7.8 (dd, J=8.6 Hz, 1.5 Hz, 1H); 7.6-7.20 (m, 4H); 7.05 (d, J=8.6 Hz, 1H); 6.8-6.3 (m, 3H); 4.5 (bs, 2H, exch. D2O).

Reference： [1]Patent: US2005/197331,2005,A1 .Location in patent: Page/Page column 16

26
[ 6293-83-0 ]
[ 536-74-3 ]
[ 6855-64-7 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 4423 - 4426
[2]Organic and Biomolecular Chemistry,2012,vol. 10,p. 8835 - 8847

27
[ 6855-64-7 ]
[ 14777-27-6 ]
N-(2-phenyl-1H-indol-5-yl)acetamidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60 - 63%		Example 5 Compound 5 N-(2-phenyl-1H-indol-5-yl)acetamidine Prepared in a manner similar to that of Example 1. Yield: (63percent); Elem. anal. C16H15N3 M.W.: 249.31; theory C, 77.08; H, 6.06; N, 16.85. found C, 76.97; H, 6.29; N, 16.85. IR (KBr): 3434, 3024, 1634, 1597 cm-1; 1H-NMR (d6-DMSO) 7.8-6.3 (m, 9H); 1.8 (s, 3H).; Example 7 Compound 5 As an alternative to the method described in Example 5, this product may be prepared as reported below: N-(2-phenyl-1H-indol-5-yl)acetamidine Prepared in a manner similar to that of Example 5. Yield: 60percent; Elem. anal. C16H15N3; theory C, 77.08; H, 6.06; N, 16.85. found C, 77.17; H, 5.89; N, 16.68. IR (KBr): 3434, 3024, 1634, 1597 cm-1; 1H-NMR (d6-DMSO) 7.8-6.3 (m, 9H); 1.8 (s, 3H).

Reference： [1]Patent: US2005/197331,2005,A1 .Location in patent: Page/Page column 15-16

28
[ 6855-64-7 ]
[ 24424-99-5 ]
(2-phenyl-5-indolyl)-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 4085 - 4093

29
N-(2-(phenylethynyl)phenyl)-4-nitrobutyramide [ No CAS ]
[ 6855-64-7 ]

Reference： [1]Patent: US2011/98311,2011,A1
[2]Patent: US2015/231142,2015,A1

30
[ 165280-21-7 ]
[ 6855-64-7 ]

Reference： [1]Patent: US2015/231142,2015,A1

31
[ 536-74-3 ]
[ 6855-64-7 ]

Reference： [1]Patent: US2015/231142,2015,A1

32
[ 6855-64-7 ]
[ 96-32-2 ]
methyl (5-amino-2-phenyl-1H-indol-1-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: 2-phenyl-1H-indol-5-amine With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 0℃; for 0.5h; Stage #2: bromoacetic acid methyl ester In N,N-dimethyl-formamide; paraffin oil at 20℃; for 20h;	35-a (Example 35-a) Methyl (5-amino-2-phenyl-1H-indol-l- yl) acetate 2-Phenyl-1H-indol-5-amine (300 mg, 1.4 mmol) was dissolved in N,N-dimethylformamide (10 mL) and cooled to0°C. To the solution was added sodium hydride (63 wt% dispersion in paraffin liquid) (75 mg, 1.7 mmcl) . The mixture was stirred for 30 mm. Then, bromoacetic acid methyl ester (0.16 ml, 1.7 mmol) was added thereto, and the mixture was stirred at room temperature for 20 h. Asaturated aqueous solution of arnmonium chloride was added to the reaction solution, followed by extraction with ethyl acetate. Then, the extract was washed with brine. The organic phase was concentrated. The obtained residue was purified by silica gel column chromatography (ethylacetate:hexane = 20:80 to 100:0) to give the title compound (270 mg, 0.96 mmcl, 67%) as an oil. LCMS (ES) : m/z 281 [M+H.

Reference： [1]Current Patent Assignee: SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE - WO2020/10252, 2020, A1 Location in patent: Page/Page column 190

33
[ 6855-64-7 ]
4-nitrophenyl [(pyridin-4-yl)methyl]carbamate [ No CAS ]
N-(2-phenyl-1H-indol-5-yl)-N’-[(pyridin-4-yl)methyl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In 1,4-dioxane at 60℃;

Reference： [1]Akiu, Mayuko; Tsuji, Takashi; Sogawa, Yoshitaka; Terayama, Koji; Yokoyama, Mika; Tanaka, Jun; Asano, Daigo; Sakurai, Ken; Sergienko, Eduard; Sessions, E. Hampton; Gardell, Stephen J.; Pinkerton, Anthony B.; Nakamura, Tsuyoshi [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 43]

34
[ 6855-64-7 ]
[ 76-05-1 ]
2-phenyl-1H-indol-5-ylammonium trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In benzene at 80℃;	2,3-Dimethyl-1-indol-5-ylammonium trifluoroacetate (3a). General procedure: Trifluoroacetic acid (0.115 g, 1.01 mmol) in benzene(10 mL) was added to a refluxing solution of 2,3-dimethyl-1-indol-5-ylamine (1a, 0.15 g, 0.94 mmol) in benzene (30 mL). The reaction mixture was cooled, the formed precipitate was filtered, washed successively with benzene and hot hexane, and dried in air.

Reference： [1]Stepanenko, I. S.; Yamashkin, S. A. [Russian Chemical Bulletin, 2022, vol. 71, # 5, p. 1043 - 1049][Izv. Akad. Nauk, Ser. Khim., 2022, # 5, p. 1043 - 1049]

35
[ 6855-64-7 ]
[ 383-63-1 ]
2,2,2-trifluoro-N-(2-phenyl-1H-indol-5-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With glacial acetic acid In benzene at 80℃; for 61h;	N-(2,3-Dimethyl-1H-indol-5-yl)-2,2,2-trifluoroacetamide (2a). General procedure: A mixture of 2,3-dimethyl-1-indol-5-ylamine (1a,0.3 g, 1.88 mmol), ethyl trifl uoroacetate (21.5 g, 0.15 mol),glacial acetic acid (a catalytic amount), and anhydrous benzene(125 mL) was refluxed on a water bath for 101 h (TLC monitoring). The solvent was evaporated, the residue was purified on a column filled with aluminium oxide using chloroform as an eluent.

Reference： [1]Stepanenko, I. S.; Yamashkin, S. A. [Russian Chemical Bulletin, 2022, vol. 71, # 5, p. 1043 - 1049][Izv. Akad. Nauk, Ser. Khim., 2022, # 5, p. 1043 - 1049]

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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 6855-64-7 ] {[proInfo.proName]}

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[ 6855-64-7 ] Synthesis Path-Upstream 1~9

[ 6855-64-7 ] Synthesis Path-Downstream 1~35

Related Functional Groups of [ 6855-64-7 ]

Aryls

Amines

Related Parent Nucleus of [ 6855-64-7 ]

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Physical hazards

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[ 6855-64-7 ]

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[ 6855-64-7 ]