1227934-69-1|Ethyl 2-bromo-4-(trifluoromethyl)oxazole-5-carboxylate| Ambeed

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Quality Control of [ 1227934-69-1 ] Purity: 95+% SDS Specification

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Product Details of [ 1227934-69-1 ]

CAS No. :	1227934-69-1
Formula :	C₇H₅BrF₃NO₃
M.W :	288.02
SMILES Code :	O=C(C1=C(C(F)(F)F)N=C(Br)O1)OCC
MDL No. :	MFCD17926293
InChI Key :	CNQYPGDMCBJWCI-UHFFFAOYSA-N
Pubchem ID :	53403202

Safety of [ 1227934-69-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1227934-69-1 ]

* 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 [ 1227934-69-1 ]

[ 1227934-69-1 ] Synthesis Path-Downstream 1~31

1
[ 110-89-4 ]
[ 1227934-69-1 ]
[ 1227934-70-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	In alpha,alpha,alpha-trifluorotoluene; at 20 - 120℃; for 0.333333h;Microwave irradiation;	Step 3: Ethyl 2-(1-piperidinyl)-4-trifluoromethyloxazole-5-carboxylate (A- 3) To a solution of <strong>[1227934-69-1]ethyl 2-bromo-4-trifluoromethyloxazole-5-carboxylate</strong> (A-2) (0.85 mL) in alpha,alpha,alpha-trifluorotoluene (10 mL) at RT was added piperidine (1.1 mL). The reaction mixture was heated at 120 0C for 20 min by microwave then cooled to RT and diluted with EtOAc (100 ml_). The organic solution was washed with H2O (2 x 100 ml_), sat. NH4CI (1 x 100 ml_), brine (1 x 100 ml_), dried over Na2SO4, filtered, and concentrated to give ethyl 2-(1 -piperidinyl)-4- trifluoromethyloxazole-5-carboxylate (A-3) as a yellow solid (1.28 g, 88% yield). LCMS (ESI) [M+1]+ 293.2.

References: [1]Patent: WO2010/59606,2010,A2 .Location in patent: Page/Page column 159-160.
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6410 - 6414.

2
[ 1569-69-3 ]
[ 1227934-69-1 ]
[ 1227935-01-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In tetrahydrofuran; at 80℃; for 5h;	Step 1 : Ethyl 2-(cyclohexylthio)-4-trif luoromethyloxazole-5-carboxylate (A-8)To compound A-2 (300 mg, 1.04 mmol) in dry THF (8 ml_) was added cyclohexanethiol (242 mg, 2.08 mmol, 0.26 ml_) and potassium carbonate (288 mg, 2.08 mmol). The resulting reaction mixture was heated at 80 0C for 5 h then cooled to RT and concentrated. Water (15 ml_) was added, and the aqueous solution was extracted with CH2CI2. The combined organic extract was dried (MgSO4), filtered, and concentrated to give the product ethyl 2- (cyclohexylthio)-4-trifluoromethyloxazole-5-carboxylate (A-8) as a yellow oil (336 mg, 100% yield). MS (M+1 ): 324.
100%	With potassium carbonate; In tetrahydrofuran; water;	Step 1: ethyl 2-(cyclohexylthio)-4-trifluoromethyloxazole-5-carboxylate (A-36) To compound A-2 (300 mg, 1.04 mmol) in dry THF (8 mL) was added cyclohexanethiol (242 mg, 2.08 mmol, 0.26 mL) and potassium carbonate (288 mg, 2.08 mmol). The resulting reaction mixture was heated at 80 C. for 5 h then cooled to RT and concentrated. Water (15 mL) was added, and the aqueous solution was extracted with CH2Cl2. The combined organic extract was dried (MgSO4), filtered, and concentrated to give the product ethyl 2-(cyclohexylthio)-4-trifluoromethyloxazole-5-carboxylate (A-36) as a yellow oil (336 mg, 100% yield). MS (M+1): 324.

References: [1]Patent: WO2010/59606,2010,A2 .Location in patent: Page/Page column 161.
[2]Patent: US2011/224137,2011,A1 .

3
[ 135026-17-4 ]
[ 1227934-69-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 0 - 20℃;Inert atmosphere;	Step 2: Ethyl 2-bromo-4-trifluoromethyloxazole-5-carboxylate (A-2) To a suspension of ethyl 2-amino-4-trifluoromethyloxazole-5-carboxylate (A-1) (9.8 g) in acetonitrile (100 ml_) at 0 C was first added copper (II) bromide (11.8 g) then te/t-butylnitrite (13.8 ml_) slowly. The reaction mixture was warmed slowly from 0 C to RT under a nitrogen atmosphere. After 4 h of stirring at RT, the reaction mixture was concentrated. The residue was suspended in EtOAc (200 ml_), washed with 1 N HCI (3 x 100 ml_), brine (1 x 100 rriL), dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash column chromatography (eluant: EtOAc and hexanes) to yield ethyl 2-bromo-4-trifluoromethyloxazole-5-carboxylate (A-2) as a colorless liquid (9.18 g, 73% yield). LCMS (ESI) [M+1]+ 288.2
52%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 0 - 20℃; for 2.5h;Inert atmosphere;	To a mixture of ethyl 2-amino-4-(trifluoromethyl)oxazole-5-carboxylate (1.8 g, 8.0 mmol, 1 eq) and CuBr2 (2.14 g, 9.6 mmol, 1.2 eq) in dry MeCN (15 mL) was added t- butylnitrite slowly. The reaction mixture was warmed slowly from 0 C to rt under a nitrogen atmosphere. After stirring at rt for 2.5 h, the mixture was diluted with saturated H4C1 aqueous solution and extracted with EA twice. The combined organic layers were dried and concentrated. The resulting residue was purified by chromatography on a silica gel column to give ethyl 2-bromo-4-(trifluoromethyl)oxazole-5-carboxylate (1.2 g, 52%) as a colorless oil.

References: [1]Patent: WO2010/59606,2010,A2 .Location in patent: Page/Page column 159.
[2]Patent: WO2018/11628,2018,A1 .Location in patent: Paragraph 00321.
[3]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6410 - 6414.

4
[ 616-45-5 ]
[ 1227934-69-1 ]
[ 1227934-97-5 ]

Yield	Reaction Conditions	Operation in experiment
34%		Step 1 : Ethyl 2-(2-oxopyrrolidin-1-yl)-4-(trifluoromethyl)oxazole-5- carboxylate (A-28)NaH (0.060 mg, 1.5 mmol) (60 %) was added to a solution of 2-oxopyrrolidine (0.13 g, 1.5 mmol) in DMF (5.0 mL) at - 78 0C followed by stirring for 15 mins at - 78 C. Then <strong>[1227934-69-1]ethyl 2-bromo-4-trifluoromethyloxazole-5-carboxylate</strong> A-2 (0.29 g, 1.0 mmol) was added. The reaction mixture was stirred for 3 h while the temperature was slowly warmed to RT. The reaction mixture was purified by chromatography on a Prep Gilson HPLC to yield ethyl 2-(2-oxopyrrolidin-1- yl)-4-(trifluoromethyl)oxazole-5-carboxylate (A-28) as a white solid (0.15 g, 34% yield). 1H NMR (500 MHz, CDCI3) delta 4.44 (m, 2H), 4.09 (t, 2H, J = 7.0 Hz), 2.69 (t, 2H1 J = 8.2 Hz), 2.28 (m, 2H), 2.42 (t, 3H, J = 7.3 Hz).

References: [1]Patent: WO2010/59606,2010,A2 .Location in patent: Page/Page column 168.

5
[ 1227934-69-1 ]
[ 1227935-03-6 ]

Yield	Reaction Conditions	Operation in experiment
88%		Step 1 : 2-Bromo-4-trifluoromethyloxazole-5-carboxylic acid (A-25)LiOH-H2O (0.64 g, 15.25 mmol) was added to a solution of ethyl 2-bromo-4- trifluoromethyloxazole-5-carboxylate (A-2) (3.50 g, 12.2 mmol) in THF/H2O (20/5 m L) at 0 0C followed by stirring for 3 h at 0 0C. The reaction mixture was diluted with EtOAc/H2O (25/25 mL) and neutralized with 1 M HCI (16 mL) at 0 0C. The organic phase was separated, dried over MgSO4, filtered, and concentrated. The product was dried in vacuo to yield 2-bromo-4- trifluoromethyloxazole-5-carboxylic acid (A-25) as a white solid (2.80 g, 88% yield).;

References: [1]Patent: WO2010/59606,2010,A2 .Location in patent: Page/Page column 167.

6
[ 35794-11-7 ]
[ 1227934-69-1 ]
[ 1227934-71-5 ]
[ 1227934-84-0 ]