914943-91-2|tert-Butyl 3-ethynylbenzoate| Ambeed

CAS No. :	914943-91-2
Formula :	C₁₃H₁₄O₂
M.W :	202.25
SMILES Code :	O=C(OC(C)(C)C)C1=CC=CC(C#C)=C1
MDL No. :	MFCD25542332
Boiling Point :	No data available
InChI Key :	SSDAUMHJIKPITN-UHFFFAOYSA-N
Pubchem ID :	71743555

Safety of [ 914943-91-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis [ 914943-91-2 ]

* 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 [ 914943-91-2 ]

[ 914943-91-2 ] Synthesis Path-Downstream 1~21

1
[ 914943-91-2 ]
[ 914942-88-4 ]
[ 914943-90-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 20 - 90℃; for 0.833333h;	Dichlorobis(triphenylphosphine)rhoalladium (104mg, 0.145mmol) was added in one portion to a mixture of A1.12 (1.Og, 2.48mmol), <strong>[914943-91-2]3-ethynyl-benzoic acid tert-butyl ester</strong> (753mg, 3.72mmol) and triethylamine (10ml) in DMF (7.0ml) at room temperature under a nitrogen atmosphere. The resulting mixture was heated to 90 0C for 50min before cooling to room temperature and evaporating in vacuo. The residue was purified by column chromatography using ethyl acetate:hexane as eluent to give 765mg (65%) of A72.1. Found: M+H = 478.21

References: [1]Patent: WO2006/122137,2006,A1 .Location in patent: Page/Page column 117.

2
[ 914943-91-2 ]
[ 1025054-94-7 ]
[ 1025053-29-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1804 - 1809.

3
[ 618-51-9 ]
[ 914943-91-2 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

4
[ 173406-17-2 ]
[ 914943-91-2 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

5
[ 914943-91-2 ]
[ 1393900-86-1 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

6
[ 914943-91-2 ]
[ 1393900-87-2 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

7
[ 914943-91-2 ]
[ 1393900-88-3 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

8
[ 914943-91-2 ]
[ 1393900-40-7 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

9
[ 914943-91-2 ]
[ 1393900-95-2 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

10
[ 914943-91-2 ]
[ 1393900-96-3 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

11
[ 914943-91-2 ]
[ 1393900-44-1 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

12
[ 914943-91-2 ]
[ 1393900-97-4 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

13
[ 914943-91-2 ]
[ 1393900-98-5 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

14
[ 914943-91-2 ]
[ 1393900-99-6 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

15
[ 914943-91-2 ]
[ 1393901-00-2 ]

References: [1]Patent: WO2012/110773,2012,A1 .
[2]Patent: WO2014/27199,2014,A1 .

16
[ 914943-91-2 ]
[ 1418731-93-7 ]

References: [1]Patent: WO2012/110773,2012,A1 .

17
[ 67-56-1 ]
[ 914943-91-2 ]
[ 10602-06-9 ]

Yield	Reaction Conditions	Operation in experiment
96%		terf-Butyl 3-ethynylbenzoate (117) (1.50 g, 9.37 mmoi) was dissolved in dry DCM (70 mL) and TFA (35.9 mL, 488 mmoi) was added carefully. The reaction was stirred at room temperature for 3 hours, concentrated in vacuo and toluene was added and then removed in vacuo to give a pale yellow solid. This material was dissolved in methanol (50 mL) and cone. H2S04 (-1 mL) was added and the resulting solution was stirred at 85 C for 20 hours. Upon cooling to room temperature, the volatiies were removed in vacuo and the residue was diluted with EtOAc (200 mL) and sat. aq. NaHCO3 (100 mL) was added slowly. The layers were separated and the aqueous layer was extracted with EtOAc (200 mL), the organic layers were combined and washed with water (100 mL), brine (100 mL), dried ( gS04), filtered and concentrated in vacuo to give the title compound (131) (1.136 g, 96% yield over 2 steps) as a pale yellow solid; 1H NMR (400 MHz, CDCI3) delta 8.17 (t, J = 1.5 Hz, 1 H), 8.03 - 8.00 (m, 1 H), 7.66 (dt, J = 7.7, 1.4 Hz, 1 H), 7.41 (td, J = 7.8, 0.4 Hz, 1 H), 3.93 (s, 3H), 3.12 (s, 1 H). LCMS Method C: rt 5.84 min.
		rert-Butyl 3-ethynylbenzoate {117) ( .50 g, 9.37 mmol) was dissolved in dry DCM (70 mL) and TFA (35.9 mL, 468 mmol) was added carefully. The reaction was stirred at room temperature for 3 hours, concentrated in vacuo and toluene was added and then removed in vacuo to give a pale yellow solid. This material was dissolved in methanol (50 mL) and cone. H2S04 (-1 mL) was added and the resulting solution was stirred at 65 C for 20 hours. Upon cooling to room temperature, the volatiles were removed in vacuo and the residue was diluted with EtOAc (200 mL) and sat. aq. NaHC03 (100 mL) was added slowly. The layers were separated and the aqueous layer was extracted with EtOAc (200 mL), the organic layers were combined and washed with water (100 mL), brine (100 mL), dried (MgS04), filtered and concentrated in vacuo to give the title compound (131) (1.136 g, 96% yield over 2 steps) as a pale yellow solid; 'H NMR (400 MHz, CDCI3) delta 8.17 (t, J = 1.5 Hz, 1 H), 8.03 - 8.00 (m, 1 H), 7.66 (dt, J = 7.7, 1.4 Hz, 1 H), 7.41 (td, J = 7.8, 0.4 Hz, 1 H), 3.93 (s, 3H), 3.12 (s, 1 H). LCMS Method C: rt 5.84 min.

References: [1]Patent: WO2014/27199,2014,A1 .Location in patent: Page/Page column 75.
[2]Patent: WO2012/110773,2012,A1 .Location in patent: Page/Page column 73.

18
[ 914943-91-2 ]
[ 1393653-50-3 ]
[ 1393900-85-0 ]

Yield	Reaction Conditions	Operation in experiment
31%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine; In N,N-dimethyl-formamide; at 120℃; for 0.416667h;microwave irradiation;	f-Butyl 3-ethynylbenzoate (117) ( .603 g, 7.93 mmol), 4-iodo-2-(methylthio)-5- (trifluoromethyl)pyrimidine (114) (1.647 g, 5.15 mmol), PdCI2(PPh3)2 (0.316 g, 0.45 mmol), PPh3 (0.355 g, 1 .35 mmol), Cu(l)l (0.232 g, 1 .22 mmol) and trethylamine (4.00 mL, 28.7 mmol) were combined in D F (20 mL) and the resulting mixture heated at 120 C under microwave irradiation for 25 minutes. The mixture was then concentrated under reduced pressure and purified twice using silica gel column chromatography ( 0-20% EtOAc/petroleum benzine 40-60 C then 50-100%DCM/petroleum benzine 40-60 CC) to give the title compound (118) (0.624 g, 31 %) as a yellow solid; 1H NMR (400 MHz, CDCI3) delta 8.73 (d, J = 0.8 Hz, 1 H), 8.25 (m, 1 H), 8.08 (m, 1 H), 7.78 (m, 1 H), 7.48 (m, 1 H), 2.63 (s, 3H), 1 .61 (s, 9H).
31%	With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 120℃; for 0.416667h;Microwave irradiation;	-Butyl 3-ethynyibenzoate (117) (1.603 g, 7.93 mmol), 4-iodo-2-(methylthio)-5- (trifiuoromethyl)pyrimidine (114) (1.647 g, 5.15 mmol), PdCI2(PPh3)2 (0.316 g, 0.45 mmoi), PPh3 (0.355 g, 1.35 mmol), Cu(i)i (0.232 g, 1.22 mmol) and trethyiamine (4.00 mL, 28.7 mmoi) were combined in D F (20 mL) and the resulting mixture heated at 120 C under microwave irradiation for 25 minutes. The mixture was then concentrated under reduced pressure and purified twice using silica gel column chromatography (10-20% EtOAc/petroleum benzine 40-60 C then 50-100% DCM/petroleum benzine 40-60 C) to give the title compound (118) (0.624 g, 31 %) as a yellow solid; 1H NMR (400 MHz, CDCI3) delta 8.73 (d, J = 0,8 Hz, H), 8.25 (m, H), 8.08 (m, 1 H), 7.78 (m, 1 H), 7.48 (m, 1 H), 2.63 (s, 3H), 1.61 (s, 9H).

References: [1]Patent: WO2012/110773,2012,A1 .Location in patent: Page/Page column 58; 61.
[2]Patent: WO2014/27199,2014,A1 .Location in patent: Page/Page column 63.

19
[ 1393900-84-9 ]
[ 914943-91-2 ]

Yield	Reaction Conditions	Operation in experiment
84%		To a solution of ferf-butyl 3-((trimethylsilyl)ethynyl)benzoate (116) (4.40 g, 16.0 mmol) in THF (100 mL) at 0 C under nitrogen was added 1.0 M TBAF in THF (20.0 mL, 20.0 mmol). The mixture was then stirred at 0 C for 1 hour then 16 hours at room temperature. The mixture was then concentrated under reduced pressure, diluted with ethyl acetate (100 mL) and washed with water (3x100 mL). The organic extract was then purified using silica gel column chromatogaphy (0-5% EtOAc/petroleum benzine 40-60 C) to give the title compound (117) (2.72 g, 84%) as a pale yellow oil; 1H NMR (400 MHz, CDCI3) delta 8.09 (dd, J = 1.5, 1.5 Hz, 1 H), 7.97 (ddd, J = 7.9, 1.5, 1.5 Hz, 1 H), 7.63 (ddd, J = 7.7, 1.4, 1.4 Hz, 1 H), 7.38 (ddd, J = 7.8, 7.8, 0.5 Hz, 1H), 3.11 (s, 1 H), 1.59 (s, 9H).
84%	With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20℃; for 17h;	To a solution of ferf-butyl 3-((trimethylsilyl)ethynyl)benzoate (116) (4.40 g, 16.0 mmol) in THF (100 mL) at 0 C under nitrogen was added 1.0 M TBAF in THF (20.0 mL, 20.0 mmo). The mixture was then stirred at 0 C for 1 hour then 16 hours at room temperature. The mixture was then concentrated under reduced pressure, diluted with ethyl acetate (100 mL) and washed with water (3x100 mL). The organic extract was then purified using silica gel column chromatogaphy (0-5% EtOAc/petroieum benzine 40-60 C) to give the title compound (117) (2.72 g, 84%) as a pale yellow oil; 1H N (400 MHz, CDCI3) delta 8.09 (dd, J = 1.5, 1.5 Hz, 1 H), 7.97 (ddd, J = 7.9, 1.5, 1.5 Hz, H), 7.63 (ddd, J = 7.7, 1.4, 1.4 Hz, 1 H), 7.38 (ddd, J = 7.8, 7.8, 0.5 Hz, 1 H), 3.11 (s, 1 H), 1.59 (s, 9H).

References: [1]Patent: WO2012/110773,2012,A1 .Location in patent: Page/Page column 58; 61.
[2]Patent: WO2014/27199,2014,A1 .Location in patent: Page/Page column 63.

20
[ 914943-91-2 ]
C₂₄H₂₅F₃N₆O [ No CAS ]

References: [1]Patent: WO2014/27199,2014,A1 .

21
[ 914943-91-2 ]
tert-butyl 3-(2,2-dibromoacetyl)benzoate [ No CAS ]

References: [1]Chemical Communications,2019,vol. 55,p. 14299 - 14302.

Historical Records

Technical Information

• Acyl Group Substitution • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Vilsmeier-Haack Reaction

Related Functional Groups of
[ 914943-91-2 ]

Aryls

A280588 [111291-97-5]

tert-Butyl 4-ethynylbenzoate

Similarity: 1.00

A190300 [10602-03-6]

Ethyl 4-ethynylbenzoate

Similarity: 0.94

A164558 [10602-06-9]

Methyl 3-ethynylbenzoate

Similarity: 0.90

A245615 [3034-86-4]

Methyl 4-ethynylbenzoate

Similarity: 0.90

A206579 [20576-82-3]

4-(tert-Butoxycarbonyl)benzoic acid

Similarity: 0.88

Alkynyls

A280588 [111291-97-5]

tert-Butyl 4-ethynylbenzoate

Similarity: 1.00

A190300 [10602-03-6]

Ethyl 4-ethynylbenzoate

Similarity: 0.94

A164558 [10602-06-9]

Methyl 3-ethynylbenzoate

Similarity: 0.90

A245615 [3034-86-4]

Methyl 4-ethynylbenzoate

Similarity: 0.90

A272766 [33577-99-0]

Methyl 2-ethynylbenzoate

Similarity: 0.83

Esters

A280588 [111291-97-5]

tert-Butyl 4-ethynylbenzoate

Similarity: 1.00

A190300 [10602-03-6]

Ethyl 4-ethynylbenzoate

Similarity: 0.94

A164558 [10602-06-9]

Methyl 3-ethynylbenzoate

Similarity: 0.90

A245615 [3034-86-4]

Methyl 4-ethynylbenzoate

Similarity: 0.90

A206579 [20576-82-3]

4-(tert-Butoxycarbonyl)benzoic acid

Similarity: 0.88

Precautionary Statements-General
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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

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Product Details of [ 914943-91-2 ]

Safety of [ 914943-91-2 ]

Application In Synthesis [ 914943-91-2 ]

[ 914943-91-2 ] Synthesis Path-Downstream 1~21

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Related Functional Groups of
[ 914943-91-2 ]

Aryls

Alkynyls

Esters

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[ 914943-91-2 ] Synthesis Path-Downstream 1~21

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