[ CAS No. 6933-49-9 ] {[proInfo.proName]}

Name: 6933-49-9|2-Methoxy-9H-carbazole|97%
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Quality Control of [ 6933-49-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6933-49-9 ]

Product Details of [ 6933-49-9 ]

CAS No. :	6933-49-9	MDL No. :	MFCD09033506
Formula :	C₁₃H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MDKVPSJRUXOFFV-UHFFFAOYSA-N
M.W :	197.23	Pubchem ID :	10797986
Synonyms :

Calculated chemistry of [ 6933-49-9 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	13
Fraction Csp3 :	0.08
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	62.3
TPSA :	25.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.1
Log Po/w (XLOGP3) :	3.36
Log Po/w (WLOGP) :	3.33
Log Po/w (MLOGP) :	2.44
Log Po/w (SILICOS-IT) :	3.57
Consensus Log Po/w :	2.96

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.75
Solubility :	0.0347 mg/ml ; 0.000176 mol/l
Class :	Soluble
Log S (Ali) :	-3.56
Solubility :	0.0539 mg/ml ; 0.000273 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.09
Solubility :	0.0016 mg/ml ; 0.00000811 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.38

Safety of [ 6933-49-9 ]

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 [ 6933-49-9 ]

* 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.

Downstream synthetic route of [ 6933-49-9 ]

[ 6933-49-9 ] Synthesis Path-Downstream 1~88

1
[ 86-79-3 ]
[ 77-78-1 ]
[ 6933-49-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; at 110℃; for 4.75h;	Example 1 l-(2-Methoxy-9H-carbazol-9-yl)-3,3-dimethylbutan-2-oneStep A. 2-Methoxy-9H-carbazole2-?ydroxycarbazole (4.83 g) was suspended in 100 mL water. A solution of 1.11 g NaOH in 100 mL water and 3.83 g dimethyl sulfate were added. The mixture was heated in 110 C oil bath for 2.5 hours. After cooling the reaction mixture was filtered. The collected solid was washed with 100 mL each of water and 0.25 M NaOH solution to give a solid. The filtrate and wash was extracted with 4x50 mL ether. This ether solution was combined with 250 mL ethyl acetate solution of the solid collected and washed with 0.2 N NaOH, water, and saturated brine to give a mixture of product and the starting material. This crude product was treated with 6 mL 5 N NaOH and 4.0 mL dimethyl sulfate in 300 mL water at 110 C for 45 minutes. Then, 12.0 mL 5 N NaOH was added and the resulting mixture stirred for 30 minutes. An additional 2.0 mL dimethyl sulfate was added and the resulting mixture heated for another hour. Repeat this sequence with 4.0 mL 5 N NaOH and 2.0 mL dimethyl sulfate. After cooling the reaction mixture, it was filtered to collect the solid product. It was washed with water and dried to give the crude product. It was purified on SGC using 30-55% EtOAc in hexanes to give the title compound as a yellow solid. 1HNMR (CD3OD, 500 MHz) ? 7.92 (d, 7.8 Hz, IH), 7.89 (d, 8.5 Hz, IH), 7.37 (d, 8.0 Hz, IH), 7.25-7.28 (m, IH), 7.08-7.11 (m, IH), 6.96 (d, 2.3 Hz, IH), 6.77 (dd, 2.3 & 8.7 Hz, IH), 3.87 (s, 3H). LC-MS: 3.31 min. (m/Z = 198.1).

Reference： [1]Journal of Organic Chemistry,1958,vol. 23,p. 524,526
[2]Patent: WO2006/44425,2006,A2 .Location in patent: Page/Page column 14 - 15

2
[ 6933-49-9 ]
[ 108-24-7 ]
[ 92438-00-1 ]

Reference： [1]Patent: DE553628,1930,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 800

3
[ 6933-49-9 ]
[ 77-78-1 ]
[ 39027-93-5 ]

Reference： [1]Patent: DE553409,1931,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 799

4
[ 3382-43-2 ]
[ 6933-49-9 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 4148 - 4159
[2]Journal of the Chemical Society,1955,p. 3475

5
[ 29511-98-6 ]
[ 6933-49-9 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 2127 - 2131
[2]Journal of Organic Chemistry,2009,vol. 74,p. 3225 - 3228
[3]European Journal of Organic Chemistry,2016,vol. 2016,p. 5611 - 5615
[4]Angewandte Chemie - International Edition,2016,vol. 55,p. 1519 - 1522
Angew. Chem.,2016,vol. 128,p. 1542 - 1545,4
[5]Green Chemistry,2017,vol. 19,p. 4798 - 4803
[6]Green Chemistry,2018,vol. 20,p. 1362 - 1366
[7]Journal of Organic Chemistry,1958,vol. 23,p. 524,526

6
[ 91901-99-4 ]
[ 6933-49-9 ]

Reference： [1]Green Chemistry,2018,vol. 20,p. 1362 - 1366
[2]European Journal of Organic Chemistry,2016,vol. 2016,p. 5611 - 5615
[3]Journal of Organic Chemistry,1957,vol. 22,p. 500
[4]Journal of the American Chemical Society,1962,vol. 84,p. 480 - 485

7
[ 67-56-1 ]
[ 3652-90-2 ]
[ 6933-49-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1231 - 1236

8
[ 51971-08-5 ]
[ 6933-49-9 ]

Reference： [1]Phytochemistry,1992,vol. 31,p. 2503 - 2506

9
[ 6933-49-9 ]
[ 111-83-1 ]
[ 116734-84-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

10
[ 6933-49-9 ]
[ 112-29-8 ]
[ 116734-85-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

11
[ 6933-49-9 ]
[ 143-15-7 ]
[ 116734-86-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

12
[ 6933-49-9 ]
[ 112-89-0 ]
[ 132901-69-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

13
[ 6933-49-9 ]
[ 75142-83-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1512 - 1515

14
[ 67-56-1 ]
[ 78863-99-7 ]
[ 41084-59-7 ]
[ 6933-49-9 ]
[ 3382-43-2 ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1231 - 1236

15
[ 67-56-1 ]
[ 3382-43-2 ]
[ 41084-59-7 ]
[ 6933-49-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1231 - 1236

16
[ 3382-43-2 ]
[ 41084-59-7 ]
[ 6933-49-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1231 - 1236
[2]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1231 - 1236

17
[ 101-16-6 ]
[ 6933-49-9 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 4614 - 4621
[2]Synlett,2006,p. 2375 - 2378
[3]Bulletin of the Chemical Society of Japan,1997,vol. 70,p. 413 - 419
[4]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1991,vol. 30,p. 247 - 251
[5]Journal of Organic Chemistry,2009,vol. 74,p. 4720 - 4726
[6]Journal of Medicinal Chemistry,2010,vol. 53,p. 5054 - 5058

18
[ 6933-49-9 ]
[ 3132-64-7 ]
1-Bromo-3-(2-methoxy-carbazol-9-yl)-propan-2-ol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 81 - 85

19
[ 101-16-6 ]
[ 6933-49-9 ]
[ 6933-50-2 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 5022 - 5028
[2]Journal of Chemical Research, Miniprint,1986,p. 2645 - 2696
[3]Journal of Chemical Research, Miniprint,1986,p. 2645 - 2696

20
4-formyl-3'-methoxydiphenylamine [ No CAS ]
[ 6933-49-9 ]
[ 6933-50-2 ]
[ 101-16-6 ]

Reference： [1]Journal of Chemical Research, Miniprint,1986,p. 2645 - 2696
[2]Journal of Chemical Research, Miniprint,1986,p. 2645 - 2696

21
[ 86-79-3 ]
[ 616-38-6 ]
[ 6933-49-9 ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 5681 - 5688

22
[ 86-79-3 ]
[ 77-78-1 ]
[ 6933-49-9 ]
[ 51846-67-4 ]
[ 39027-93-5 ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 5681 - 5688

23
[ 109-65-9 ]
[ 6933-49-9 ]
9-n-butyl-2-methoxycarbazole [ No CAS ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 5681 - 5688

24
[ 20013-55-2 ]
[ 6933-49-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With triethyl phosphite; for 16h;Heating / reflux;	Synthesis example 11 2-methoxycarbazole 8.36 g (36.7 mmol) 4'-methoxy-2-nitro-1,1'-biphenyl in 40 ml triethylphosphite is refluxed during 16 hours in argon atmosphere. The mixture was allowed to cool to room temperature, upon which the product precipitates. Filtration and washing with methanol gave 6.67 g (93 %) of a white solid 1H NMR (DMSO-d6): delta11.10 (s, 1H), 8.00 (dd, J=1.5 Hz, J=8 Hz, 1H), 7.8 (d, J=8 Hz, 1H), 7.44 (dd, J=1.5 Hz, J=8 Hz, 1H), 7.30 (dt, J=1.5 Hz, J=8 Hz, 1H), 7.12 (dt, J=1.5 Hz, J=8 Hz, 1H), 6.98 (d, J=1.5 Hz, 1H), 6.78 (dd, J=1.5 Hz, J=8 Hz, 1H), 3.83 (s, 3H). 13C NMR (DMSO-d6): delta 158, 141, 140, 124, 123, 121, 119, 118, 116, 111, 108, 94, 55. mp: 239 C.
70%		In a 500 mL round-bottom flask was added 4?-methoxy-2-nitro-1,1?-biphenyl (10.3 g, 44.7 mmol) and triethyl phosphite (44.2 mL, 258 mmol). The reaction mixture was heated to reflux at 165 C. in an oil bath under nitrogen for 18 hours. The reaction mixture was cooled to room temperature and 60 mL of 6 N HCl was added dropwise over a period of 30 min. with continuous stirring (exothermic reaction). After the addition, the reaction was heated for 3 hours at 80 C., resulting in the formation of copious precipitate. After cooling to room temperature, water was added (100 mL) and the reaction mixture was neutralized with 50% NaOH (aq.) (60-70 mL, exothermic reaction). The resulting mixture was extracted with 3×250 mL EtOAc and the combined organic layers were washed with brine, dried over Na2SO4, filtered and solvent removed under reduced pressure. To this was added 5-10 mL DCM and the insoluble solid was filtered and washed with hexane to give 6.2 g (70%) of 2-methoxy-9H-carbazole as a light yellow solid. The product was confirmed by GC/MS and NMR.

Reference： [1]Patent: EP1838671,2008,B1 .Location in patent: Page/Page column 11; 12
[2]European Journal of Organic Chemistry,2016,vol. 2016,p. 2096 - 2100
[3]Patent: US9461254,2016,B2 .Location in patent: Page/Page column 186-187
[4]Physical Chemistry Chemical Physics,2017,vol. 19,p. 6721 - 6730
[5]Synlett,2005,p. 127 - 133
[6]Heterocycles,1998,vol. 48,p. 1513 - 1518
[7]European Journal of Organic Chemistry,2016,vol. 2016,p. 5474 - 5479
[8]Chemistry - A European Journal,2018,vol. 24,p. 11278 - 11282

Yield	Reaction Conditions	Operation in experiment
71%		Example 3 2-Methoxy-9H-carbazole A solution of 1a (14.7 g, 64.1 mmol) in triethyl phosphite (50 mL) was refluxed for 4 h, and then cooled to room temperature. The resulting precipitate was collected by filtration and rinsed with Et2 O. The filtrate was rinsed with 1N HCl (2*250 mL), and the resulting precipitate in the organic extract was collected by filtration and combined with the previously obtained precipitate to furnish a white solid (9.0 g, 71% yield): mp 223-225 C.; ?Cummins, J. A.; Tomlinson, M. L., J. Chem. Soc., 3475-7[(1955)]1 H NMR (DMSO-d6) delta11.11 (s, 1H), 7.97 (d, 1H, J=8.4 Hz), 7.95 (d, 1H, J=8.4 Hz), 7.42 (d, 1H, J=7.8 Hz), 7.27 (t, 1H, J=8.1 Hz), 7.09 (t, 1H, J =7.8 Hz), 6.95 (s, 1H), 6.75 (d, 1H, J=8.4 Hz), 3.82 (s, 3H); 13 C NMR (DMSO-d6) delta158.49, 141.10, 139.72, 124.11, 122.66, 120.89, 119.24, 118.53, 116.17, 110.60, 107.69, 94.43, 55.24. Anal. Calcd for C13 H11 NO.0.1H2 O: C, 78.45; H, 5.67; N, 7.04. Found: C, 78.54; H, 5.87; N, 6.77.
	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 60℃;Schlenk technique;	General procedure: In a 10 mL Schlenk tube,The compound (1-4) (0.2 mmol, 39.5 mg) was added,Grubbs-II catalyst (CAS: 246047-72-3) (2 mol%, 5.3 mg)And toluene (15 mL).The reaction mixture was allowed to react at 60 C,TLC was detected until the reaction was complete. The reaction mixture was washed with saturated sodium bicarbonate (20 mL x 2) and extracted with EA (20 mL x 2). The combined organic phases were washed with saturated NaCl (20 mL x 1). After separation, the mixture was dried over anhydrous magnesium sulfate and the organic solvent was removed under reduced pressure. The purified product was purified by silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 3: 1]White solid, yield: 75%.

27
[ 86-79-3 ]
MeX [ No CAS ]
[ 6933-49-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1512 - 1515

28
[ 16098-16-1 ]
[ 6933-49-9 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 5014 - 5019
[2]Journal of Organic Chemistry,2012,vol. 77,p. 1663 - 1674
[3]Organic Letters,2004,vol. 6,p. 533 - 535

29
[ 6933-49-9 ]
[ 1147550-11-5 ]
2-methoxy-3-thiocyanato-9<i>H</i>-carbazole [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 5831 - 5834

30
(2-iodo-phenyl)-(3-methoxy-phenyl)-amine [ No CAS ]
[ 6933-49-9 ]
[ 6933-50-2 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 347 - 355

31
[ 16098-16-1 ]
[ 6933-49-9 ]
[ 38088-00-5 ]

Reference： [1]Advanced Synthesis and Catalysis,2007,vol. 349,p. 713 - 718

32
[ 615-43-0 ]
[ 6933-49-9 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 347 - 355
[2]Green Chemistry,2017,vol. 19,p. 4798 - 4803
[3]Organic Letters,2018,vol. 20,p. 216 - 219

33
[ 217813-03-1 ]
[ 6933-49-9 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 347 - 355

34
[ 5344-78-5 ]
[ 6933-49-9 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 5014 - 5019
[2]Journal of Organic Chemistry,2012,vol. 77,p. 1663 - 1674

35
[ 98-80-6 ]
[ 6933-49-9 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 5014 - 5019
[2]Synlett,2005,p. 127 - 133
[3]Journal of Organic Chemistry,2012,vol. 77,p. 1663 - 1674
[4]European Journal of Organic Chemistry,2016,vol. 2016,p. 5611 - 5615
[5]Green Chemistry,2018,vol. 20,p. 1362 - 1366

36
[ 104-92-7 ]
Mo(CO)6 [ No CAS ]
[ 6933-49-9 ]

Reference： [1]Synlett,2005,p. 127 - 133

37
[ 5570-19-4 ]
[ 6933-49-9 ]

Reference： [1]Synlett,2005,p. 127 - 133

38
[ 132993-22-7 ]
[ 6933-49-9 ]

Reference： [1]Heterocycles,1998,vol. 48,p. 1513 - 1518
[2]Heterocycles,1998,vol. 48,p. 1513 - 1518

39
[ 88-75-5 ]
diazotized 2-amino-<1>naphthylmercury-acetate [ No CAS ]
[ 6933-49-9 ]

Reference： [1]Heterocycles,1998,vol. 48,p. 1513 - 1518
[2]Heterocycles,1998,vol. 48,p. 1513 - 1518

40
[ 2398-37-0 ]
[ 6933-49-9 ]

Reference： [1]Journal of Chemical Research, Miniprint,1986,p. 2645 - 2696

41
[ 103-84-4 ]
N-phenyl-N'-acetyl-urea [ No CAS ]
[ 6933-49-9 ]

Reference： [1]Journal of Chemical Research, Miniprint,1986,p. 2645 - 2696

42
[ 101651-37-0 ]
[ 6933-49-9 ]

Reference： [1]Journal of Chemical Research, Miniprint,1986,p. 2645 - 2696

43
[ 6933-49-9 ]
1-tert-Butylamino-3-(2-methoxy-carbazol-9-yl)-propan-2-ol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 81 - 85

44
[ 78863-99-7 ]
[ 6933-49-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1231 - 1236
[2]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1231 - 1236

45
[ 24224-28-0 ]
[ 6933-49-9 ]

Reference： [1]Phytochemistry,1992,vol. 31,p. 2503 - 2506

46
[ 6933-49-9 ]
[ 116734-97-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

47
[ 6933-49-9 ]
[ 116734-98-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

48
[ 6933-49-9 ]
[ 116734-99-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

49
[ 6933-49-9 ]
[ 116734-81-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

50
[ 6933-49-9 ]
[ 116734-82-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

51
[ 6933-49-9 ]
[ 116734-83-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

52
[ 6933-49-9 ]
[ 132901-71-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

53
[ 6933-49-9 ]
[ 132901-70-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

54
[ 6933-49-9 ]
[ 132901-73-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

55
[ 6933-49-9 ]
[ 113864-38-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

56
[ 6933-49-9 ]
[ 116753-48-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

57
[ 6933-49-9 ]
[ 113864-46-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

58
[ 6933-49-9 ]
[ 116734-91-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

59
[ 6933-49-9 ]
[ 116734-92-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

60
[ 6933-49-9 ]
[ 113864-49-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

61
[ 6933-49-9 ]
[ 132901-72-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1575 - 1579

62
[ 99970-47-5 ]
[ 6933-49-9 ]

Reference： [1]Journal of Organic Chemistry,1958,vol. 23,p. 524,526

63
[ 6933-49-9 ]
[ 51846-67-4 ]

Reference： [1]Patent: DE553409,1931,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 799

64
[ 13314-79-9 ]
[ 6933-49-9 ]

Reference： [1]Journal of the Chemical Society,1955,p. 3475

65
[ 38088-00-5 ]
[ 6933-49-9 ]

Reference： [1]Journal of the American Chemical Society,1962,vol. 84,p. 480 - 485
[2]European Journal of Organic Chemistry,2016,vol. 2016,p. 5611 - 5615
[3]Green Chemistry,2018,vol. 20,p. 1362 - 1366

66
[ 6933-49-9 ]
[ 5469-26-1 ]
[ 885130-72-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 1.5h;	Step B. l-(2-Methoxy-9H-carbazol-9-yl)-3,3-dimethylbutan-2-oneTo a solution of 29.6 mg <strong>[6933-49-9]2-methoxy-9H-carbazole</strong> from the Step A above in 1 mL anhydrous DMF was added 7 mg NaH (60% oil dispersion). After a few minutes, 29.5 mg of l-bromo-3,3-dimethylbutan-2- one was added. After 1.5 hours at room temperature, the reaction mixture was placed in a refrigerator over night. It was purified on RP-HPLC using 55-100% MeCN gradient in water with 0.1% TFA to give the title compound as a colorless solid after lyophilization. LC-MS: 3.82 min. (m/Z = 296.3, 210.2,318.2).

Reference： [1]Patent: WO2006/44425,2006,A2 .Location in patent: Page/Page column 14; 15

67
[ 6933-49-9 ]
[ 105-36-2 ]
C₁₇H₁₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at 40℃;	N,N-Dibutyl-2-(2-methoxy-9H-carbazol-9-yl)acetamide Step A. (2-Methoxy-9H-carbazol-9-yl)acetic acidTo a solution of 0.56 g <strong>[6933-49-9]2-methoxy-9H-carbazole</strong> from the Step A Example 1 in 15 mL anhydrous DMF was added 0.125 g ?a? (60% oil dispersion). After 5 minutes, 0.53 g ethyl bromoacetate was added to the reaction mixture and the resulting mixture was heated in 40C oil bath. The reaction mixture was cooled to room temperature and 1 mL water was added very carefully followed by 1 niM 5 NaOH. The resulting mixture was heated in 4OC oil bath for 30 minutes when BDPLC analysis indicated hydrolysis had completed. Solvents were removed under reduced pressure. The residue was partitioned between 50 mL each of water and EtOAc. The layers were separated and the organic layer was extracted with 0.2 NaOH twice. The combined aqueous layers were acidified with concentrated HCl to pH ~1 and extracted with EtOAc several times. The combine EtOAc extract was washed with saturated brine, dried over anhydrous Na2SO4, and evaporated to give the crude product. The latter was purified on RP-?PLC to give the title compound as a yellow solid. 1H NMR (CDCl3, 500 MHz) ? .01 (d, 7.6 Hz, IH), 7.98 (d, 8.7 Hz, IH), 7.40-7.43 (m, IH), 7.25-7.31 (m, 2H), 7.90 (dd, 8.5 & 2.3 Hz, IH), 6.81 (d, 2.3 Hz, IH), 5.01 (s, 2H), 3.94 (s, 3H). LC-MS: 3.11 min. (m/Z = 256.2, 210.2).

Reference： [1]Patent: WO2006/44425,2006,A2 .Location in patent: Page/Page column 14; 16

68
[ 6933-49-9 ]
[ 1647-23-0 ]
[ 885130-73-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at 40℃; for 20h;	Example 2 9-(3,3-Dimethylbutyl)-<strong>[6933-49-9]2-methoxy-9H-carbazole</strong>To a solution of 29.6 mg <strong>[6933-49-9]2-methoxy-9H-carbazole</strong> from the Step A Example 1 in 1 mL anhydrous DMF was added 7 mg NaH (60% oil dispersion). After a few minutes, 27.2 mg of l-bromo-3,3-dimethylbutane was added and the reaction mixture was heated in a 40 C oil bath for 20 hours. It was purified on RP- HPLC using 70~100% MeCN gradient in water with 0.1% TFA to give the title compound as a colorless solid after lyophilization. LC-MS: 4.48 min. (m/Z = 282.3, 198.2).

Reference： [1]Patent: WO2006/44425,2006,A2 .Location in patent: Page/Page column 14; 15 - 16

69
[ 6933-49-9 ]
[ 890079-77-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In tetrahydrofuran; at 0 - 20℃;	Synthesis example 12 3-bromo-<strong>[6933-49-9]2-methoxycarbazole</strong> In a flask, covered with aluminium foil, a stirred solution of 6.62 g (33.6 mmol) <strong>[6933-49-9]2-methoxycarbazole</strong> in 150 ml tetrahydrofuran was cooled to 0 C. 5.38 g (30.2 mmol) N-bromosuccinimide was added in small portions. The mixture was allowed to warm to room temperature overnight. THF was evaporated and the product was used without further purification. 1H NMR (DMSO-d6): delta 11.30 (s, 1H), 8.34 (s, 1H), 8.04 (dd, J=1.5 Hz, J=8 Hz, 1H), 7.46 (dd, J=1.5 Hz, J=8 Hz, 1H), 7.33 (dt, J=1.5 Hz, J=8 Hz, 1H), 7.14 (dt, J=1.5 Hz, J=8 Hz, 1H), 7.14 (s, 1H), 3.93 (s, 3H). 13C NMR (DMSO-d6): delta 153, 140, 139, 124, 124, 122, 120, 119, 116, 110, 101, 95, 56.

Reference： [1]Patent: EP1838671,2008,B1 .Location in patent: Page/Page column 12

70
[ 591-50-4 ]
[ 6933-49-9 ]
[ 1357929-88-4 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 1663 - 1674

71
[ 6933-49-9 ]
[ 1357929-89-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 1663 - 1674

72
[ 92023-24-0 ]
[ 6933-49-9 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 2127 - 2131

73
[ 38089-03-1 ]
[ 6933-49-9 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 1903 - 1907
[2]Organic Letters,2015,vol. 17,p. 1597 - 1600
[3]European Journal of Organic Chemistry,2016,vol. 2016,p. 5474 - 5479
[4]European Journal of Organic Chemistry,2012,p. 2127 - 2131
[5]Organic Letters,2014,vol. 16,p. 2892 - 2895
[6]Angewandte Chemie - International Edition,2016,vol. 55,p. 1519 - 1522
Angew. Chem.,2016,vol. 128,p. 1542 - 1545,4
[7]Advanced Synthesis and Catalysis,2016,vol. 358,p. 3145 - 3151
[8]European Journal of Organic Chemistry,2016,vol. 2016,p. 5611 - 5615
[9]European Journal of Organic Chemistry,2016,vol. 2016,p. 5611 - 5615
[10]Green Chemistry,2017,vol. 19,p. 4798 - 4803
[11]Organic Letters,2018,vol. 20,p. 216 - 219
[12]Green Chemistry,2018,vol. 20,p. 1362 - 1366

74
[ 5720-07-0 ]
[ 6933-49-9 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 2127 - 2131
[2]European Journal of Organic Chemistry,2012,p. 2127 - 2131
[3]Organic Letters,2014,vol. 16,p. 2892 - 2895
[4]Angewandte Chemie - International Edition,2016,vol. 55,p. 1519 - 1522
Angew. Chem.,2016,vol. 128,p. 1542 - 1545,4
[5]European Journal of Organic Chemistry,2016,vol. 2016,p. 5611 - 5615
[6]European Journal of Organic Chemistry,2016,vol. 2016,p. 5611 - 5615
[7]Patent: US9461254,2016,B2
[8]Green Chemistry,2017,vol. 19,p. 4798 - 4803
[9]Physical Chemistry Chemical Physics,2017,vol. 19,p. 6721 - 6730
[10]Organic Letters,2018,vol. 20,p. 216 - 219
[11]Green Chemistry,2018,vol. 20,p. 1362 - 1366
[12]Chemistry - A European Journal,2018,vol. 24,p. 11278 - 11282

75
[ 95-50-1 ]
[ 6933-49-9 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 2127 - 2131
[2]European Journal of Organic Chemistry,2012,p. 2127 - 2131

76
[ 26595-63-1 ]
[ 88284-48-4 ]
[ 6933-49-9 ]
[ 6933-50-2 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 2968 - 2971
Angew. Chem.,2013,vol. 125,p. 3041 - 3044

77
[ 586-96-9 ]
4-methoxy-2-(trimethylsilyl)phenyl triflate [ No CAS ]
[ 18992-85-3 ]
[ 6933-49-9 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 2968 - 2971
Angew. Chem.,2013,vol. 125,p. 3041 - 3044

78
[ 40999-06-2 ]
[ 6933-49-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,2013,vol. 50,p. 91 - 98

79
[ 1451423-08-7 ]
[ 6933-49-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,2013,vol. 50,p. 91 - 98

80
[ 197292-94-7 ]
[ 6933-49-9 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 3473 - 3475
[2]Organic Letters,2018,vol. 20,p. 216 - 219

81
[ 481071-90-3 ]
[ 6933-49-9 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 3473 - 3475

82
[ 74447-76-0 ]
[ 6933-49-9 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 3473 - 3475

83
[ 6933-49-9 ]
[ 2404-36-6 ]
9-cycloheptyl-2-methoxy-9H-carbazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 5129 - 5133
Angew. Chem.,2013,vol. 125,p. 5233 - 5237,7

84
[ 1609211-13-3 ]
[ 6933-49-9 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2892 - 2895

85
[ 615-36-1 ]
[ 6933-49-9 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2892 - 2895
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 1519 - 1522
Angew. Chem.,2016,vol. 128,p. 1542 - 1545,4
[3]European Journal of Organic Chemistry,2016,vol. 2016,p. 5611 - 5615
[4]European Journal of Organic Chemistry,2016,vol. 2016,p. 5611 - 5615
[5]Green Chemistry,2018,vol. 20,p. 1362 - 1366

86
[ 5720-07-0 ]
[ 615-36-1 ]
[ 6933-49-9 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1597 - 1600

87
[ 808758-81-8 ]
[ 6933-49-9 ]
C₄₅H₃₃N₃O₃ [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 83122 - 83128

88
[ 808758-81-8 ]
[ 6933-49-9 ]
C₄₆H₃₅N₃O₂ [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 83122 - 83128

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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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H412	Harmful to aquatic life with long-lasting effects
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 6933-49-9 ] {[proInfo.proName]}

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[ 6933-49-9 ] Synthesis Path-Downstream 1~88

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