[ CAS No. 2199-49-7 ] {[proInfo.proName]}

Name: 2199-49-7|Ethyl 4-methyl-1H-pyrrole-3-carboxylate|97%
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Quality Control of [ 2199-49-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2199-49-7 ]

Product Details of [ 2199-49-7 ]

CAS No. :	2199-49-7	MDL No. :	MFCD00030417
Formula :	C₈H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MMDOYVVZUVZLHQ-UHFFFAOYSA-N
M.W :	153.18	Pubchem ID :	235044
Synonyms :

Calculated chemistry of [ 2199-49-7 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.38
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.85
TPSA :	42.09 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	1.29
Log Po/w (WLOGP) :	1.5
Log Po/w (MLOGP) :	0.71
Log Po/w (SILICOS-IT) :	2.01
Consensus Log Po/w :	1.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.74
Solubility :	2.78 mg/ml ; 0.0182 mol/l
Class :	Very soluble
Log S (Ali) :	-1.77
Solubility :	2.58 mg/ml ; 0.0168 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.46
Solubility :	0.532 mg/ml ; 0.00348 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.68

Safety of [ 2199-49-7 ]

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 [ 2199-49-7 ]

* 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 [ 2199-49-7 ]
Downstream synthetic route of [ 2199-49-7 ]

[ 2199-49-7 ] Synthesis Path-Upstream 1~1

1
[ 2199-49-7 ]
[ 40318-15-8 ]

Reference： [1] Gazzetta Chimica Italiana, 1955, vol. 85, p. 1378,1392[2] Annali di Chimica (Rome, Italy), 1956, vol. 46, p. 847,855

[ 2199-49-7 ] Synthesis Path-Downstream 1~88

1
2-bromo-5-iodo-4-methyl-pyrrole-3-carboxylic acid ethyl ester [ No CAS ]
[ 2199-49-7 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 5295,5297

2
[ 90610-58-5 ]
[ 2199-49-7 ]

Reference： [1]Tetrahedron,1990,vol. 46,p. 7599 - 7659
[2]Journal of the American Chemical Society,1944,vol. 66,p. 1137,1143
[3]Gazzetta Chimica Italiana,1955,vol. 85,p. 1378,1392
Annali di Chimica (Rome, Italy),1956,vol. 46,p. 847,855

3
[ 2199-49-7 ]
[ 37789-74-5 ]
[ 132281-91-5 ]
[ 37789-70-1 ]

Reference： [1]Tetrahedron,1990,vol. 46,p. 7599 - 7659

4
[ 2199-49-7 ]
[ 68-12-2 ]
[ 6339-66-8 ]

Yield	Reaction Conditions	Operation in experiment
80%		Step 1 : Ethyl 5-formyl-4-methyl-1 H-pyrrole-3-carboxylate (3a) The Vilsmeier reagent was prepared by treatment of dry DMF (19.0 g, 261 mmol) with POCI3 (40.0 g, 261 mol) at 0C and stirred for another hour at rt. In a flask, a solution of ethyl 4-methyl-1 H-pyrrole-3-carboxylate (26.6 g, 174 mmol) in dry DMF (50 mL) was treated with the freshly prepared Vilsmeier reagent at 0C. The resulting mixture was stirred for another hour at rt, then poured into ice, adjusted the pH to 7-8 with 10N NaOH, heated to 60C for 2 h and then cooled. The yellow precipitate was collected by filtration, redissolved in EA, washed with brine, dried over Na2S04, filtered and concentrated to give compound 3a (25.3 g, 80%) as a yellow solid.

Reference： [1]Molecules,2011,vol. 16,p. 9368 - 9385
[2]Patent: WO2014/23367,2014,A1 .Location in patent: Page/Page column 75
[3]Journal of Organic Chemistry,2010,vol. 75,p. 1016 - 1039
[4]Journal of Organic Chemistry,2017,vol. 82,p. 9350 - 9359
[5]Journal of the Chemical Society. Perkin transactions I,1987,p. 1383 - 1388
[6]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 2153 - 2157

5
[ 2199-49-7 ]
[ 1989-53-3 ]
[ 79205-16-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 667 - 670

6
[ 6277-13-0 ]
[ 2199-49-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 1383 - 1388
[2]Journal of Porphyrins and Phthalocyanines,2010,vol. 14,p. 89 - 100

7
[ 38622-91-2 ]
[ 623-70-1 ]
[ 2199-49-7 ]
4-Methyl-3H-pyrrole-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1983,vol. No. 1,p. 26 - 27

8
4-Methyl-3H-pyrrole-3-carboxylic acid ethyl ester [ No CAS ]
[ 2199-49-7 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1983,vol. No. 1,p. 26 - 27

9
[ 925430-09-7 ]
[ 2199-49-7 ]
1-cyclopropyl-4-methylpyrrole-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 44 - 45

10
[ 2199-49-7 ]
sodium dihydrobis(2-methoxyehtoxy aluminate) [ No CAS ]
[ 822-51-5 ]

Yield	Reaction Conditions	Operation in experiment
	In water; benzene;	Preparation of 3,4-Dimethylpyrrole. To a solution of 23 g (80 mmoles) of sodium dihydrobis(2-methoxyehtoxy aluminate) was added dropwise of a solution of 5 g (34 mmoles) of ethyl 4-methylpyrrol-3-carboxylate in 50 mL of benzene at room temperature under nitrogen atmosphere. The reaction mixture was stirred for 18 h. Water (100 mL) was added to the reaction mixture. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed and the residue was distilled giving 1.2 g (44%) of the title compound.

Reference： [1]Patent: US6846839,2005,B1

11
[ 2199-49-7 ]
[ 442563-21-5 ]

Reference： [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 2153 - 2157

12
[ 2199-49-7 ]
[ 442563-22-6 ]

Reference： [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 2153 - 2157

13
[ 2199-49-7 ]
4-(3-chloro-4-fluoro-phenylamino)-5-[3-methyl-4-(4-methyl-piperazine-1-carbonyl)-1<i>H</i>-pyrrol-2-ylmethylene]-5,7-dihydro-pyrrolo[2,3-<i>d</i>]pyrimidin-6-one [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 2153 - 2157

14
[ 2199-49-7 ]
[ 172270-39-2 ]

Reference： [1]Heterocycles,1995,vol. 41,p. 2553 - 2564

15
[ 2199-49-7 ]
2-ethoxycarbonyl-3,7,8,12,13,17,18,22,23-nonamethylpentaphyrin [ No CAS ]

Reference： [1]Heterocycles,1995,vol. 41,p. 2553 - 2564

16
[ 623-70-1 ]
n-Bu₂Cu(CN)Li₂ [ No CAS ]
[ 2199-49-7 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1983,vol. No. 1,p. 26 - 27

17
[ 2199-49-7 ]
[ 112306-32-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 1383 - 1388

18
[ 2199-49-7 ]
[ 79205-21-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 667 - 670

19
[ 2199-49-7 ]
[ 79205-14-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 667 - 670

20
[ 2199-49-7 ]
[ 79205-18-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 667 - 670

21
[ 2199-49-7 ]
[ 79205-23-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 667 - 670

22
[ 2199-49-7 ]
[ 79205-25-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 667 - 670

23
[ 2199-49-7 ]
ethyl 2-chloro-5-formyl-4-methyl-1H-pyrrole-3-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 2089,2093
[2]Journal of the American Chemical Society,1953,vol. 75,p. 2089,2093
[3]Molecules,2011,vol. 16,p. 9368 - 9385

24
[ 2199-49-7 ]
2-bromo-5-formyl-4-methyl-pyrrole-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 2089,2093
[2]Journal of the American Chemical Society,1953,vol. 75,p. 2089,2093

25
[ 2199-49-7 ]
[ 859067-05-3 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 2089,2093

26
[ 90346-74-0 ]
[ 2199-49-7 ]

Reference： [1]Gazzetta Chimica Italiana,1955,vol. 85,p. 1378,1392
Annali di Chimica (Rome, Italy),1956,vol. 46,p. 847,855

27
[ 90561-96-9 ]
[ 2199-49-7 ]

Reference： [1]Gazzetta Chimica Italiana,1955,vol. 85,p. 1378,1392
Annali di Chimica (Rome, Italy),1956,vol. 46,p. 847,855
[2]Journal of the American Chemical Society,1953,vol. 75,p. 5295,5297

28
[ 100129-92-8 ]
[ 2199-49-7 ]

Reference： [1]Gazzetta Chimica Italiana,1955,vol. 85,p. 1378,1392
Annali di Chimica (Rome, Italy),1956,vol. 46,p. 847,855

29
[ 4458-69-9 ]
[ 2199-49-7 ]

Reference： [1]Gazzetta Chimica Italiana,1955,vol. 85,p. 1378,1392
Annali di Chimica (Rome, Italy),1956,vol. 46,p. 847,855
[2]Journal of the American Chemical Society,1953,vol. 75,p. 5295,5297

30
[ 5448-15-7 ]
[ 2199-49-7 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 5295,5297

31
[ 37789-75-6 ]
[ 2199-49-7 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 5295,5297

32
[ 5448-16-8 ]
[ 2199-49-7 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1137,1143

33
[ 2199-49-7 ]
sodium dihydrobis(2-methoxyethoxy aluminate) [ No CAS ]
[ 19713-89-4 ]

Yield	Reaction Conditions	Operation in experiment
	In water; benzene;	To a solution of 23 g (80 mmoles) of sodium dihydrobis(2-methoxyethoxy aluminate) was added dropwise of a solution of 5 g (34 mmoles) of ethyl 4-methylpyrrol-3-carboxylate in 50 mL of benzene at room temperature under nitrogen atmosphere. The reaction mixture was stirred for 18 h. Water (100 mL) was added to the reaction mixture. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed and the residue was distilled giving 1.2 g (44%) of the title compound. Preparation of 3,4-Dimethylpyrrole-2-carboxaldehyde.
	In water; benzene;	To a solution of 23 g (80 mmoles) of sodium dihydrobis(2-methoxyethoxy aluminate) was added dropwise of a solution of 5 g (34 mmoles) of ethyl 4-methylpyrrol-3-carboxylate in 50 mL of benzene at room temperature under nitrogen atmosphere. The reaction mixture was stirred for 18 h. Water (100 mL) was added to the reaction mixture. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed and the residue was distilled giving 1.2g (44%) of the title compound. Preparation of 3,4-Dimethylpyrrole-2-carboxaldehyde.

Reference： [1]Patent: US5883116,1999,A
[2]Patent: US5834504,1998,A

34
[ 2199-49-7 ]
[ 98-88-4 ]
ethyl 5-benzoyl-4-methyl-1H-pyrrole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	tin(IV) chloride; In dichloromethane; water;	EXAMPLE 89 Ethyl 4-Methyl-5-benzoylpyrrole-3-carboxylate Ethyl 4-methylpyrrole-3-carboxylate (920 mg., 6 mmoles) was combined with benzoyl chloride (0.7 ml., 6 mmoles), stannic chloride (1.2 ml., 12 mmoles) in 25 ml. of methylene chloride and stirred under nitrogen for 2 hours at room temperature. Water (15 ml.) was added slowly, dissolving the precipitate which had formed. Ether (50 ml.) was then added, and the organic phase separated, back-washed with 20 ml. of water, and evaporated to an oil. The oil was triturated with hexane to yield crystalline product (1.12 g.). Recrystallization from acetone/hexane afforded purified ethyl 4-methyl-5-benzoylpyrrole-3-carboxylate (900 mg., m.p. 127-129 C.).
0.81 g	With zinc(II) chloride; In 1,2-dichloro-ethane; at 90℃; for 4.5h;	To a solution of Compound I (1.0 g) in 1,2-dichloroethane (20 mL) were added benzoyl chloride (1.4 mL) and zinc chloride (1.8 g), and the mixture was heated to reflux at 90C for 4.5 hours. The reaction solution was diluted with chloroform, and then thereto was added 2N aqueous sodium hydroxide solution, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 3/1) to give Compound II (0.81 g).

Reference： [1]Patent: US4282242,1981,A
[2]Patent: EP2612848,2013,A1 .Location in patent: Paragraph 0367; 0368; 0369

35
[ 2199-49-7 ]
[ 2199-54-4 ]

Yield	Reaction Conditions	Operation in experiment
70%		EXAMPLE 38 2,4,5-Trimethyl-3-carbethoxy-pyrrole STR46 As in Example 32 but using 3-methyl-4-carbethoxy-pyrrole9). The product (70%) formed colourless needles, m.p. 103-105 unchanged on admixture with the product of Example 39 below. 9) H. Fischer and H. Orth, loc. cit. p. 246.

Reference： [1]Patent: US4070366,1978,A

36
[ 2199-49-7 ]
[ 455-13-0 ]
[ 875657-48-0 ]

Reference： [1]Patent: WO2006/13939,2006,A1 .Location in patent: Page/Page column 43-44

37
[ 2199-49-7 ]
[ 1227469-95-5 ]

Reference： [1]Journal of Porphyrins and Phthalocyanines,2010,vol. 14,p. 89 - 100

38
[ 2199-49-7 ]
[ 68-12-2 ]
[ 442563-21-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With trichlorophosphate; In dichloromethane; at 50℃;Cooling with ice;	To the ice-cold solution of DMF (600 mg, 8.22 mmol) and POCl3 (1.0 g, 6.54 mmol) in dichloromethane (DCM, 5 mL) was added a solution of ethyl 4-methyl-lH-pyrrole-3- carboxylate (500 mg, 3.27 mmol) in DCM (10 mL). The reaction solution was stirred at 50 0C for 30 minutes and cooled with ice bath. To this solution was slowly added a solution of NaHCO3 (sat.) to adjust pH to 7 before extracting two times with 50 mL of EtOAc. The organic layers were combined, washed twice with brine (100 mL), dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography eluted with ethyl acetate - petroleum ether (1 : 20) to afford 5-formyl-4-methyl-lH-pyrrole- 3-carboxylate as a white solid (0.5 g, 85%). MS m/z: 182 [M+l] + .

Reference： [1]Patent: WO2009/139834,2009,A1 .Location in patent: Page/Page column 100

39
[ 2199-49-7 ]
[ 1196886-65-3 ]

Reference： [1]Patent: WO2009/139834,2009,A1

40
[ 2199-49-7 ]
[ 1196882-75-3 ]

Reference： [1]Patent: WO2009/139834,2009,A1

41
[ 2199-49-7 ]
(Z)-5-((2-amino-4-chloro-6-oxo-7-(pyridin-3-ylmethyl)-6,7-dihydropyrrolo[2,3-d]pyrimidin-5-ylidene)methyl)-1H-pyrrole-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2009/139834,2009,A1

42
[ 2199-49-7 ]
[ 1196885-87-6 ]

Reference： [1]Patent: WO2009/139834,2009,A1

43
[ 2199-49-7 ]
(Z)-5-((2-amino-4-chloro-6-oxo-7-(pyridin-2-ylmethyl)-6,7-dihydropyrrolo[2,3-d]pyrimidin-5-ylidene)methyl)-1H-pyrrole-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2009/139834,2009,A1

44
[ 2199-49-7 ]
[ 1196885-85-4 ]

Reference： [1]Patent: WO2009/139834,2009,A1

45
[ 2199-49-7 ]
(Z)-5-((2-amino-4-chloro-6-oxo-7-(pyridin-4-ylmethyl)-6,7-dihydropyrrolo[2,3-d]pyrimidin-5-ylidene)methyl)-1H-pyrrole-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2009/139834,2009,A1

46
[ 2199-49-7 ]
[ 1196885-83-2 ]

Reference： [1]Patent: WO2009/139834,2009,A1

47
[ 2199-49-7 ]
(Z)-5-((2-amino-4-chloro-7-((1-methyl-1H-pyrazol-3-yl)methyl)-6-oxo-6,7-dihydropyrrolo[2,3-d]pyrimidin-5-ylidene)methyl)-1H-pyrrole-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2009/139834,2009,A1

48
[ 2199-49-7 ]
[ 1196885-89-8 ]

Reference： [1]Patent: WO2009/139834,2009,A1

49
[ 2199-49-7 ]
(Z)-5-((2-amino-4-chloro-7-((4.5-dimethylthiazol-2-yl)methyl)-6-oxo-6,7-dihydropyrrolo[2,3-d]pyrimidin-5-ylidene)methyl)-1H-pyrrole-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2009/139834,2009,A1

50
[ 2199-49-7 ]
[ 1196885-91-2 ]

Reference： [1]Patent: WO2009/139834,2009,A1

51
[ 2199-49-7 ]
[ 1316844-31-1 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 4324 - 4327

52
[ 2199-49-7 ]
[ 1316844-44-6 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 4324 - 4327

53
[ 2199-49-7 ]
[ 1316844-56-0 ]
[ 1316844-57-1 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 4324 - 4327

54
[ 2199-49-7 ]
[ 74-88-4 ]
[ 1316844-19-5 ]

Yield	Reaction Conditions	Operation in experiment
4.9 g		To a stirred solution of <strong>[2199-49-7]ethyl 4-methylpyrrole-3-carboxylate</strong> (Alfa Aesar, 5 g, 32.6 mmol) in DMF (100 mL) was added NaH (1.567 g, 39.2 mmol) at 0C under Ar. The reaction mixture wasstirred for 30 mm at rt. Mel (2.449 mL, 39.2 mmol) was added. The reaction mixture was stirred for 30 mm at rt, quenched by addition of a saturated aqueous solution of NaHCO3 (75 mL), and extracted with EtOAc (2 x 75 mL). The combined organic extracts were washed with a saturated aqueous solution of NaHCO3 (75 mL), dried (Na2SO4), filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (2.5-12.5% EtOAc/hexane) toafford the title compound (4.9 g) as a colorless oil. Rf = 0.23 (10% EtOAc/hexane); Rt: 0.92 mm (LC-MS 1); MS mlz: 168.1 [M+H](LC-MS 1).

Reference： [1]Organic Letters,2011,vol. 13,p. 4324 - 4327
[2]Patent: WO2015/75665,2015,A1 .Location in patent: Page/Page column 90

55
[ 2199-49-7 ]
[ 66022-60-4 ]
C₁₃H₂₀N₂O₄ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 11127 - 11130

56
[ 2199-49-7 ]
[ 102-96-5 ]
ethyl 4-methyl-5-(2-nitro-1-phenylethyl)-1H-pyrrole-3-carboxylate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 11127 - 11130

57
[ 2199-49-7 ]
[ 1196887-75-8 ]

Reference： [1]Molecules,2011,vol. 16,p. 9368 - 9385

58
[ 2199-49-7 ]
[ 1355372-18-7 ]

Reference： [1]Molecules,2011,vol. 16,p. 9368 - 9385

59
[ 2199-49-7 ]
[ 1355372-19-8 ]

Reference： [1]Molecules,2011,vol. 16,p. 9368 - 9385

60
[ 2199-49-7 ]
[ 1355372-01-8 ]

Reference： [1]Molecules,2011,vol. 16,p. 9368 - 9385

61
[ 2199-49-7 ]
[ 1355372-02-9 ]

Reference： [1]Molecules,2011,vol. 16,p. 9368 - 9385

62
[ 10544-63-5 ]
[ 38622-91-2 ]
[ 2199-49-7 ]

Reference： [1]Molecules,2011,vol. 16,p. 9368 - 9385

63
[ 2199-49-7 ]
[ 1313196-90-5 ]

Reference： [1]Patent: EP2518054,2012,A1

64
[ 2199-49-7 ]
[ 1313196-92-7 ]

Reference： [1]Patent: EP2518054,2012,A1

65
[ 2199-49-7 ]
[ 1207970-76-0 ]
[ 1313196-91-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine;copper diacetate; at 50 - 80℃; for 6h;	A mixture of <strong>[2199-49-7]ethyl 4-methyl-1H-pyrrole-3-carboxylate</strong> (184 mg, 1.2 mmol), 4,4,5,5-tetramethyl-2-[2-[3-(trifluoromethyl)benzyl]-1-benzothiophen-7-yl]-1,3,2-dioxaborolane (602 mg, 1.44 mmol), copper acetate (109 mg, 0.6 mmol) and pyridine (6.0 mL) was stirred for 2 hr at 50C, and stirred for 4 hr at 80C. The reaction mixture was allowed to cool to room temperature, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 95:5?90:10) to give crude ethyl 4-methyl-1-[2-[3-(trifluoromethyl)benzyl]-1-benzothiophen-7-yl]-1H-pyrrole-3-carboxylate (84 mg). To a solution of the compound (84 mg) in THF (2 mL)-methanol (1 mL) was added 2N aqueous sodium hydroxide solution (284 muL, 0.568 mmol), and the mixture was stirred for 2 hr.at room temperature. 2N Aqueous sodium hydroxide solution (0.5 mL, 1.00 mmol) was added thereto. The mixture was stirred for 1.5 hr at room temperature, stirred for 1 hr at 50C, and heated under reflux overnight. The reaction mixture was acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give crude 4-methyl-1-[2-[3-(trifluoromethyl)benzyl]-1-benzothiophen-7-yl]-1H-pyrrole-3-carboxylic acid (80 mg). A solution of the obtained crude 4-methyl-1-[2-[3-(trifluoromethyl)benzyl]-1-benzothiophen-7-yl]-1H-pyrrole-3-carboxylic acid (80 mg), glycinamide hydrochloride (25 mg, 0.227 mmol), WSC (44 mg, 0.227 mmol), HOBt (31 mg, 0.227 mmol) and N,N-diisopropylethylamine (39 muL, 0.227 mmol) in DMF (2.0 mL) was stirred for 5 hr at room temperature. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol= 100:0?95:5) and NH silica gel column chromatography (ethyl acetate:methanol= 95:5). The obtained crystals were recrystallized from hexane-ethyl acetate to give the title compound (27 mg, yield 5%, 3 steps) as crystals. melting point 152-153C. 1H-NMR (CDCl3) delta: 2.39 (3 H, s), 4.14 (2 H, d, J = 5.2 Hz), 4.28 (2 H, s), 5.40 (1 H, br s), 6.24 (1 H, br s), 6.43 - 6.54 (1 H, m), 6.89 - 6.96 (1 H, m), 7.11 (1 H, s), 7.21 (1 H, dd, J = 7.6, 0.7 Hz), 7.39 (1 H, t, J = 7.8 Hz), 7.43 - 7.57 (4 H, m), 7.58 (1 H, d, J = 2.5 Hz), 7.65 (1 H, d, J = 7.4 Hz).

Reference： [1]Patent: EP2518054,2012,A1 .Location in patent: Page/Page column 73; 74

66
[ 2199-49-7 ]
[ 1361938-27-3 ]

Reference： [1]Patent: EP2612848,2013,A1

67
[ 2199-49-7 ]
[ 1361938-28-4 ]

Reference： [1]Patent: EP2612848,2013,A1

68
[ 2199-49-7 ]
5-benzoyl-N-(5-hydroxyadamantan-2-yl)-1,4-dimethyl-1H-pyrrole-3-carboxamide [ No CAS ]

Reference： [1]Patent: EP2612848,2013,A1

69
[ 2199-49-7 ]
[ 22385-77-9 ]
[ 1561964-22-4 ]