[ CAS No. 1200828-74-5 ] {[proInfo.proName]}

Name: 1200828-74-5|Ethyl 2-bromo-2-cyclopropylacetate|95%
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SKU: A636646
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Quality Control of [ 1200828-74-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1200828-74-5 ]

CAS No. :	1200828-74-5	MDL No. :	MFCD18837719
Formula :	C₇H₁₁BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BTAPHOMYBWYDEU-UHFFFAOYSA-N
M.W :	207.07	Pubchem ID :	44222804
Synonyms :

Calculated chemistry of [ 1200828-74-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.86
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.8
TPSA :	26.3 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) :	-6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.37
Log Po/w (XLOGP3) :	2.05
Log Po/w (WLOGP) :	1.66
Log Po/w (MLOGP) :	1.73
Log Po/w (SILICOS-IT) :	1.97
Consensus Log Po/w :	1.96

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.15
Solubility :	1.46 mg/ml ; 0.00706 mol/l
Class :	Soluble
Log S (Ali) :	-2.23
Solubility :	1.22 mg/ml ; 0.00588 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.87
Solubility :	2.81 mg/ml ; 0.0136 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.56

Safety of [ 1200828-74-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3265
Hazard Statements:	H302-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1200828-74-5 ]

* 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 [ 1200828-74-5 ]

[ 1200828-74-5 ] Synthesis Path-Downstream 1~37

1
[ 1185387-66-9 ]
[ 1200828-74-5 ]

Yield	Reaction Conditions	Operation in experiment
	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; for 2h;	A flame dried two-neck round bottom flask fitted with a reflux condenser and N2 outlet was charged with anhydrous THF, freshly activated Mg (120 mg, 4.95 mmol) and a catalytic amount of iodine. A small portion of cyclopropyl bromide dissolved in THF was added. Afier initiation of reflux, the reaction mixture was cooled to -20 C. and the remaining cyclopropyl bromide (500 mg, 4.13 mmol) was gradually added. Afier 30 mm a freshly distilled solution of glyoxalate 45 (549 mg, 5.37 mmol) in THF was added over a 10 mm period and the resulting solution was stirred at -20 C. for 2 h before being quenched with a small amount of watet After 10 mm the reaction mixture was thrther diluted with water (50 mL) and extracted with ethyl acetate (3x50 mL). The organic extracts were combined, dried over anhydrous Mg504, filtered, concentrated in vacuo and purifiedby column chromatography eluting with ethyl acetate/nhexane (a gradient of 10-20%) to furnish ethyl a-hydroxy132 cyclopropaneacetate (422 mg, 71%) as a viscous oil. The oil (350 mg, 2.43 mmol) was dissolved in anhydrous DCM and cooled to 0 C. Then Ph3P (2.04 gm, 7.78 mmol) was added followed by C13r4 (1.20 gm, 3.64 mmol). The reactionmixture was stirred at 0 C. for 2 h and then concentrated in vacuo. The Ph3PO was precipitated by addition of n-hexane and removed by filtration. The crude reaction mixture was purified by flash column chromatography to furnish ethyl a-bromocyclopropaneacetate (46, R=c-Pr): (311 mg, 62%yield).

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 4623 - 4630
[2]Chemistry - A European Journal,2018,vol. 24,p. 2059 - 2064
[3]Patent: US10125116,2018,B2 .Location in patent: Page/Page column 131; 132

2
[ 90-15-3 ]
[ 1200828-74-5 ]
[ 1185387-69-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;	To a solution of 1-naphthol (170 mg, 1.18 mmol) in anhydrous DMF (10 mL) was added K2CO3 (510 mg, 3.53 mmol) and ethyl alpha-bromocyclopropaneacetate (295 mg, 1.41 mmol). The mixture was stirred at room temperature for 2 h and then diluted with water (50 mL) and then extracted with ethyl acetate (3*50 mL). The organic extracts were combined, washed with brine, dried over anhydrous MgSO4, filtered, concentrated in vacuo and purified by flash column chromatography using a mixture of ethyl acetate and n-hexane (1:9) to furnish ethyl 2-cyclopropyl-2-(1-naphthalenyloxy)acetate (8, R=c-Pr, 296 mg, 93%) as a white solid. The ester (250 mg, 0.92 mmol) was dissolved in 20 mL THF: H2O (2:1) and then 3M NaOH (111 mg, 2.77 mmol) was added. The reaction was heated at 80 C. for 6 h. After cooling, the reaction mixture was quenched with 1N HCL to a pH ?7 and then extracted with chloroform. The organic extract was dried over anhydrous MgSO4, filtered, concentrated in vacuo and purified by flash column chromatography eluting with a mixture of ethyl acetate/n-hexane (a gradient of 2:1) to furnish 2-cyclopropyl-2-(1-naphthalenyloxy)acetic acid (41, R=c-Pr) (136 mg, 61%) as a white solid.

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 4623 - 4630
[2]Patent: US10125116,2018,B2 .Location in patent: Page/Page column 5; 132

3
CBr₄ [ No CAS ]
[ 4333-56-6 ]
[ 1200828-74-5 ]

Yield	Reaction Conditions	Operation in experiment
62%	With triphenylphosphine;iodine; In tetrahydrofuran; hexane; ethyl alpha-hydroxycyclopropaneacetate; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran;	Example 2 Synthesis of ethyl alpha-bromocyclopropaneacetate (46, R=c-Pr) A flame dried two-neck round bottom flask fitted with a reflux condenser and N2 outlet was charged with anhydrous THF, freshly activated Mg (120 mg, 4.95 mmol) and a catalytic amount of iodine. A small portion of cyclopropyl bromide dissolved in THF was added. After initiation of reflux, the reaction mixture was cooled to -20 C. and the remaining cyclopropyl bromide (500 mg, 4.13 mmol) was gradually added. After 30 min a freshly distilled solution of glyoxylate 45 (549 mg, 5.37 mmol) in THF was added over a 10 min period and the resulting solution was stirred at -20 C. for 2 h before being quenched with a small amount of water. After 10 min the reaction mixture was further diluted with water (50 mL) and extracted with ethyl acetate (3*50 mL). The organic extracts were combined, dried over anhydrous MgSO4, filtered, concentrated in vacuo and purified by column chromatography eluting with ethyl acetate/n-hexane (a gradient of 10-20%) to furnish ethyl alpha-hydroxycyclopropaneacetate (422 mg, 71%) as a viscous oil. The oil (350 mg, 2.43 mmol) was dissolved in anhydrous DCM and cooled to 0 C. Then Ph3P (2.04 gm, 7.78 mmol) was added followed by CBr4 (1.20 gm, 3.64 mmol). The reaction mixture was stirred at 0 C. for 2 h and then concentrated in vacuo. The Ph3PO was precipitated by addition of n-hexane and removed by filtration. The crude reaction mixture was purified by flash column chromatography to furnish ethyl alpha-bromocyclopropaneacetate (46, R=c-Pr): (311 mg, 62% yield).

Reference： [1]Patent: US2012/101096,2012,A1

4
[ 64-17-5 ]
[ 5239-82-7 ]
[ 1200828-74-5 ]

Yield	Reaction Conditions	Operation in experiment
70%		Step 1. ethyl bromo(cyclopropyl)acetate Thionyl chloride (0.46 mL, 6.3 mmol) was added dropwise to a solution of cyclopropylacetic acid (0.5 g, 5 mmol) (Oakwood cat003710) in 1,2-dichloroethane (5.2 mL) at room temperature. The reaction was heated to reflux for 2 h then allowed to cool to room temperature, at which time N-bromosuccinimide (1.12 g, 6.27 mmol) and hydrogen bromide (2 mu, 0.04 mmol) (48% aqueous solution) were added successively. The resulting mixture was heated to reflux for 2 days. The reaction mixture was then cooled to room temperature, ethanol (4 mL) was added, and the reaction was stirred at room temperature for an additional 2 h. The reaction mixture was then concentrated to afford the crude product. The crude product was dissolved in carbon tetrachloride and was passed through a short column of silica gel and concentrated to afford ethyl bromo(cyclopropyl)acetate (0.70 g, 70%) as an oil.
		Racemic ethyl 2-bromo-2-cyclopropylacetate The above compound was prepared by adding a solution of 2-cyclopropylacetic acid (24.7 g, 247 mmol) in anhydrous DCE (250 mL) to thionyl chloride (22 mL, 302 mmol) dropwise over 5 minutes at 25 C. After refluxing for 2 hours, the reaction was cooled to room temperature, and N-bromosuccinimde (53.6 g, 301 mmol) and hydrogen bromide (48% aqueous solution; 0.195 mL, 1.727 mmol) were added successively at 25 C. The mixture was refluxed for 3 days, then cooled to room temperature. Absolute EtOH (200 mL) was added and the resulting dark brown solution was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure and the residue was suspended in carbon tetrachloride (300 mL) and filtered through a glass filter. The filtrate was concentrated under the reduced pressure. The crude product was purified by flash chromatography (silica-gel, 330 g x 2, 5 % ethyl acetate in hexanes) to provide ethyl 2-bromo-2-cyclopropylacetate. .H NMR (400 MHz, CDCk) delta ppm 4.24 (m, 2 H), 3.58 (d, J=12.0 Hz, 1H), 1.58 (m, 1H), 0.90-0.80 (m, 2 H), 0.53 (m, 1H), 0.42 (m, 1H), 1.3 (t, J = 8.0 Hz, 3 H).

Reference： [1]Patent: WO2015/164480,2015,A1 .Location in patent: Page/Page column 52
[2]Patent: WO2013/49250,2013,A1 .Location in patent: Page/Page column 293; 294

5
[ 1200828-74-5 ]
[ 1429385-24-9 ]
ethyl 2-((2R,3R)-2-(3-chlorophenyl)-3-(4-chlorophenyl)-5-oxomorpholino)-2-cyclopropylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step A. Ethyl 2-((2i?,3i?)-2-(3-chlorophenyl)-3-(4-chlorophenyl)-5-oxomorpholino)-2- cyclopropylacetate The above compound was prepared according to the following procedure: To a solution of (5i?,6i?)-6-(3-chlorophenyl)-5-(4-chlorophenyl)morpholin-3-one (4.3 g, 13.35 mmol) (Example 1 12, Step A) in DMF (26.7 mL) was added sodium hydride (1.068 g, 26.7 mmol) at 0 C and the mixture was stirred at this temperature for 30 minutes. To the mixture was added racemic <strong>[1200828-74-5]ethyl 2-bromo-2-cyclopropylacetate</strong> (3.71 mL, 26.7 mmol) in DMF (40 mL) dropwise and the mixture was stirred at room temperature for 2 hours. The reaction was quenched with sat. NH4CI (10 mL) and diluted with diethyl ether (10 mL). The solution was washed with 10% citric acid (10 mL), 5% NaHC03 (10 mL), water (10 mL), brine (10 mL), then dried with MgS04. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (120 g) eluting with 20% to 50% acetone in hexanes ethyl 2-((2i?,3i?)-2-(3-chlorophenyl)-3-(4-chlorophenyl)-5-oxomorpholino)-2- cyclopropylacetate as a 1.2: 1 mixture of epimers which were taken into the next step as a mixture. Mass spectrum (ESI) m/z = 448.0 [M - H]+.

Reference： [1]Patent: WO2013/49250,2013,A1 .Location in patent: Page/Page column 294; 295

6
[ 1200828-74-5 ]
[ 1429385-24-9 ]
[ 1429386-05-9 ]
[ 1429386-06-0 ]

Reference： [1]Patent: WO2013/49250,2013,A1

7
[ 1200828-74-5 ]
[ 1429385-24-9 ]
[ 1429386-03-7 ]
[ 1429386-04-8 ]

Yield	Reaction Conditions	Operation in experiment
		Sodium hydride (60% dispersion in mineral oil, 1.07 g, 26.7 mmol) was added to a solution of (5R,6R)-6-(3-chlorophenyl)-5-(4-chlorophenyl)morpholin-3-one (4.3 g, 13.4 mmol, Example 1, Step A) in dimethylformamide (26.7 mL) at 0 C, and the mixture was stirred at this temperature for 30 minutes. Racemic <strong>[1200828-74-5]ethyl 2-bromo-2-cyclopropylacetate</strong> (preparation described above, 3.71 mL, 26.7 mmol) in dimethylformamide (40 mL) was added dropwise and the mixture was stirred at room temperature for 2 hours. The reaction was quenched with saturated ammonium chloride (10 mL) and diluted with diethyl ether (10 mL). The solution was washed with 10% citric acid (10 mL), 5% NaHC03 (10 mL), water (10 mL), and brine (10 mL), and then dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash chromatography on silica gel (120 g, gradient elution of 20% to 50% acetone in hexanes) to provide the title compounds as a 1.2: 1 mixture of diastereomers. MS (ESI) m/z: 448.0 [M + H]+ for both isomers.

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2472 - 2488
[2]Patent: WO2014/151863,2014,A1 .Location in patent: Page/Page column 49; 50

8
[ 1200828-74-5 ]
6-(3-chlorophenyl)-5-(4-chlorophenyl)morpholin-3-one [ No CAS ]
ethyl 2-(2-(3-chlorophenyl)-3-(4-chlorophenyl)-5-oxomorpholino)-2-cyclopropylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step B. (i?)-Ethyl 2-((25',3i?)-2-(3-chlorophenyl)-3-(4-chlorophenyl)-5-oxomorpholino)- 2-cyclopropylacetate and (5)-ethyl 2-((2i?,3S)-2-(3-chlorophenyl)-3-(4-chlorophenyl)-5- oxomorpholino)-2-cyclopropylacetate or (S)-ethyl 2-((25',3i?)-2-(3-chlorophenyl)-3-(4- chlorophenyl)-5-oxomorpholino)-2-cyclopropylacetate and (i?)-ethyl 2-((2i?,3S)-2-(3- chlorophenyl)-3- 4-chlorophenyl)-5-oxomorpholino)-2-cyclopropylacetate Sodium hydride (150 mg, 3.72 mmol, 60% dispersion in oil) was added to a stirring solution of (5i?,65)-6-(3-chlorophenyl)-5-(4-chlorophenyl)morpholin-3-one and (55*,6i?)- 6-(3-chlorophenyl)-5-(4-chlorophenyl)morpholin-3-one (1.0 g, 3.14 mmol, Example 11, Step D) in DMF (7.5 mL). The reaction was stirred for 10 minutes, at room temperature and treated with (±)-<strong>[1200828-74-5]ethyl 2-bromo-2-cyclopropylacetate</strong> (707 mg, 3.41 mmol, Example 69, Step A). After 16 hours the reaction was treated with NH4C1 (saturated aqueous solution) and ethyl acetate. The separated organic layer was washed with 1.0 M aqueous LiCl, dried over MgS04, filtered and evaporated under reduced pressure. Flash column chromatography (silica gel; gradient elution with 1 :0 to 2: 1 hexanes:ethyl acetate) gave one pair of the the title compounds as the first eluting isomers. 1H NMR (500 MHz, CDC13, delta ppm): 7.16 - 7.20 (m, 1H), 7.11 (dd, J= 8.4, 7.0 Hz, 3H), 6.95 (t, J= 2.0 Hz, 1H), 6.81 (dt, J= 7.6, 1.7 Hz, 1H), 6.76 (d, J= 8.3 Hz, 2H), 5.24 - 5.28 (m, 1H), 4.90 (d, J= 2.7 Hz, 1H), 4.70 (d, J= 17.4 Hz, 1H), 4.56 (d, J= 17.4 Hz, 1H), 4.34 (d, J= 10.5 Hz, 1H), 4.27 (q, J= 7.1 Hz, 2H), 1.34 (t, J= 7.2 Hz, 3H), 0.46 - 0.68 (m, 3H), -0.09 - 0.02 (m, 1H), -0.32 - -0.23 (m, 1H).

Reference： [1]Patent: WO2014/130470,2014,A1 .Location in patent: Page/Page column 224-225

9
[ 53432-87-4 ]
[ 1200828-74-5 ]

Yield	Reaction Conditions	Operation in experiment
		Step A. Ethyl 2-bromo-2-cyclopropylacetate Methyl 2-cyclopropylacetate (4 g, 35 mmol) in THF (10 mL) was added dropwise over 5 minutes to a stirring solution of LDA (23 mL, 35 mmol, 1.8 M solution) in THF (80 mL) at -78 C. The reaction was stirred at this temperature for 20 minutes, and then trimethylchlorosilane (7 mL, 53 mmol) was added dropwise over 2 minutes. The reaction was stirred at -78 C for 20 minutes, and a solution of NBS (14 g, 77 mmol) in THF (10 mL) was added dropwise over 3 minutes. The reaction was allowed to warm to room temperature overnight. The reaction was treated with ethyl acetate and water. The separated organic layer was washed with brine, dried over MgS04, filtered and evaporated under a vacuum. Flash column chromatography (80 g, Si02, gradient elution with 1 :0 to 1 : 1 hexanes: ethyl acetate) gave the racemic title compound. 1H NMR (400 MHz, CDC13, delta ppm): 4.26 (q, J= 7.1 Hz, 2H), 3.45 (d, J= 10.4 Hz, 1H), 1.54 - 1.66 (m, 1H), 1.24 - 1.36 (m, 3H), 0.79 - 0.89 (m, 2H), 0.50 - 0.60 (m, 1H), 0.39 - 0.49 (m, 1H).

Reference： [1]Patent: WO2014/130470,2014,A1 .Location in patent: Page/Page column 223-224

10
[ 5239-82-7 ]
[ 1200828-74-5 ]

Reference： [1]Patent: WO2014/151863,2014,A1

11
[ 54322-65-5 ]
[ 1200828-74-5 ]

Reference： [1]Patent: WO2014/151863,2014,A1

12
[ 1010802-72-8 ]
[ 64-17-5 ]
[ 1200828-74-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 20℃; for 1h;	Absolute ethanol (200 mL) was added and the resulting dark brown solution was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in carbon tetrachloride (300 mL) and filtered through a glass filter. The filtrate was concentrated under the reduced pressure. The resulting product was purified by flash chromatography (silica gel, two 330 g columns, eluent: 5% ethyl acetate in hexanes) to provide racemic ethyl 2-bromo-2- cyclopropylacetate. 1H NMR (400 MHz, CDCl3, delta, ppm): 4.24 (m, 2H), 3.58 (d, J=12.0 Hz, 1H), 1.58 (m, 1H), 0.90-0.80 (m, 2H), 0.53 (m, 1H), 0.42 (m, 1H), 1.3 (t, j = 8.0 Hz, 3H).

Reference： [1]Patent: WO2014/151863,2014,A1 .Location in patent: Page/Page column 48; 49

13
[ 81721-87-1 ]
[ 1200828-74-5 ]
C₁₅H₁₆N₂O₆ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 222 - 236

14
[ 1914-02-9 ]
[ 1200828-74-5 ]
ethyl 2-cyclopropyl-2-(3,3-dimethylindolin-1-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
162 mg	With potassium carbonate; In acetonitrile; at 100℃; for 16h;	A mixture of 3,3-dimethylindoline (105 mg, 0.713 mmol), <strong>[1200828-74-5]ethyl 2-bromo-2-cyclopropylacetate</strong> (297 muL, 2.143 mmol), and potassium carbonate (300 mg, 2.171 mmol) in 2 mL CH3CN was stirred at 100C (oil bath) for 16 h. The mixture was extracted with 2 M HC1 and CH2C12. Organic phases were concentrated and residue was purified by preparative HPLC. Fractions containing product were partly concentrated and the residue was extracted with 1 M NaHC03and CH2C12. Organic phases were dried over MgS04, filtered, and concentrate to give ethyl 2-cyclopropyl-2-(3,3-dimethylindolin-l-yl)acetate (162 mg) as a brownish oil. LCMS m/z = 274.4 [M+l]+; NMR (400 MHz, CDC13) delta ppm 0.37-0.43 (m, 1H), 0.52-0.58 (m, 1H), 0.61-0.73 (m, 2H), 1.20 (t, J = 7.1 Hz, 3H), 1.26-1.34 (m, 7H), 3.33 (d, J = 9.4 Hz, 1H), 3.49 (d, J = 8.4 Hz, 1H), 3.61 (d, J = 8.4 Hz, 1H), 4.13 (q, J = 7.1 Hz, 2H), 6.30 (dd, J1= 7.5 Hz, J2= 0.8 Hz, 1H), 6.63-6.67 (m, 1H), 6.98-7.02 (m, 2H).

Reference： [1]Patent: WO2015/66344,2015,A1 .Location in patent: Page/Page column 241

15
[ 1200828-74-5 ]
2-cyclopropyl-2-(3,3-dimethylindolin-1-yl)ethanol [ No CAS ]

Reference： [1]Patent: WO2015/66344,2015,A1

16
[ 1200828-74-5 ]
2-(2-cyclopropyl-2-(3,3-dimethylindolin-1-yl)ethyl)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Patent: WO2015/66344,2015,A1

17
[ 1200828-74-5 ]
C₁₅H₂₂N₂ [ No CAS ]

Reference： [1]Patent: WO2015/66344,2015,A1

18
[ 1200828-74-5 ]
[ 106-47-8 ]
C₁₃H₁₆ClNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In ethanol; at 50℃; for 16h;	A mixture of <strong>[1200828-74-5]ethyl 2-bromo-2-cyclopropylacetate</strong> 187A (3.0 g, 14.5 mmol), 4- chloroaniline (1.8 g, 14.5 mmol), and NaHCO3(3.7 g, 43.5 mmol) in ethanol (100 mL) was stirred at 50oC for 16 hours. The mixture was evaporated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 20% v/v) to give Compound 187B. LC-MS (ESI) m/z: 254 [M+H]+;1H- NMR (CDCl3, 400 MHz): delta (ppm) 0.35-0.59 (m, 4H), 0.85-0.87 (m, 1H), 1.26 (t, J = 7.2 Hz, 3H), 1.55 (t, J = 7.2 Hz, 1H), 4.18-4.26 (m, 3H), 6.51 (d, J = 6.8 Hz, 2H), 7.10 (d, J = 6.8 Hz, 2H).

Reference： [1]Patent: WO2017/214505,2017,A1 .Location in patent: Paragraph 000887; 000888

19
[ 1200828-74-5 ]
1-(2-aminobenzo[d]thiazol-6-yl)-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]inden-4-ol [ No CAS ]
Ethyl 2-((1-(2-aminobenzo[d]thiazol-6-yl)-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]inden-4-yl)oxy)-2-cyclopropylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%		Step 2: Ethyl 2-((1-(2-aminobenzo[d]thiazol-6-yl)-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]inden-4-yl)oxy)-2-cyclopropylacetate The title compound (117, 43% yield) was prepared from 1-(2-aminobenzo[d]thiazol-6-yl)-7,8,9,10-tetrahydro-6-oxa-2,10a-diazacycloocta[cd]inden-4-ol and <strong>[1200828-74-5]ethyl 2-bromo-2-cyclopropylacetate</strong> following a procedure analogous to Example 279, Step 1. LCMS (ESI): [M+H]+=479.