98968-72-0|tert-Butyl (2-fluorophenyl)carbamate| Ambeed

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Quality Control of [ 98968-72-0 ] Purity: 98% SDS Specification

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Product Details of [ 98968-72-0 ]

CAS No. :	98968-72-0
Formula :	C₁₁H₁₄FNO₂
M.W :	211.23
SMILES Code :	O=C(OC(C)(C)C)NC1=CC=CC=C1F
MDL No. :	MFCD04112559
InChI Key :	AUHNQFOFWVWFTH-UHFFFAOYSA-N
Pubchem ID :	4935500

Safety of [ 98968-72-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 98968-72-0 ]

* 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 [ 98968-72-0 ]

[ 98968-72-0 ] Synthesis Path-Downstream 1~38

1
[ 98968-72-0 ]
[ 870-63-3 ]
N-tert-butoxycarbonyl-6-fluoro-2-(3,3-dimethylallyl)aniline [ No CAS ]

References: [1]Heterocycles,1993,vol. 36,p. 2051 - 2058.

2
[ 6940-76-7 ]
[ 98968-72-0 ]
[ 121006-55-1 ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 5725 - 5728.

3
[ 79099-07-3 ]
[ 98968-72-0 ]
C₁₇H₂₁FN₂O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 657 - 661.

4
[ 98968-72-0 ]
[ 154150-27-3 ]
{2-[2-Benzenesulfinyl-2-(tert-butyl-dimethyl-silanyl)-ethyl]-6-fluoro-phenyl}-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Heterocycles,1994,vol. 38,p. 45 - 50.

5
[ 98968-72-0 ]
[ 95-92-1 ]
(2-tert-Butoxycarbonylamino-3-fluoro-phenyl)-oxo-acetic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 7303 - 7306.

6
[ 98968-72-0 ]
[ 74-88-4 ]
[ 138343-78-9 ]

References: [1]Synthesis,1991,p. 871 - 878.

7
[ 348-54-9 ]
[ 24424-99-5 ]
[ 98968-72-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 20℃; for 6h;Heating / reflux;	tert-Butyl 2-fluorophenylcarbamate; To a solution of di-tert-butyldicarbonate (45.2 g, 207 mmol, 1.0 equiv) in tetrahydrofuran (210 mL) at room temperature was added 2-fluoroaniline (20.0 mL, 207 mmol). The reaction was heated to reflux and held there for 6h. It was cooled, concentrated, dissolved in pentane, washed with 5% citric acid, then 1 M potassium bisulfate (2x), then water, then 20% potassium hydroxide, then brine, dried over magnesium sulfate, and concentrated to give 48.0 g (quant) as an amber oil which was used without purification.'H-NMR (CDC13, 500 MHz) 8 1.52 (s, 9H), 6.68 (bs, 1H), 6.85-7. 20 (m, 3H), 8.07 (dd, J=8. 1,8. 1,1H). Mass spec.: 234.18 (MNa) +.
98.9%	In tetrahydrofuran; at 25 - 80℃; for 12h;	To a solution of 2-fluoroaniline (C1.1-a) (25 g, 225 mmol, 1.0 equiv) in THF (300 mL) was added Boc2O (73.6 g, 337 mmol, 77.5 mL, 1.5 equiv) at 25C, and then stirred at 80C for 12h. The reaction mixture was concentrated under reduced pressure to give tert-butyl N-(2- fluorophenyl) carbamate (C1.1-b) (47 g, 223 mmol, 98.90% yield) as colorless oil. 1H NMR (DMSO-d6, 400MHz) δ8.98 (s, 1H), 7.68-7.60 (m, 1H), 7.27-7.10 (m, 3H), 1.50 (s, 9H)
98.90%	In tetrahydrofuran; at 25 - 80℃; for 12h;	To a solution of 2-fluoroaniline (1.1-a) (25 g, 225 mmol, 1.0 equiv) in THF (300 mL) was added Boc2O (73.6 g, 337 mmol, 77.5 mL, 1.5 equiv) at 25C, and then stirred at 80C for 12 h. The reaction mixture was concentrated under reduced pressure to give tert-butyl N-(2-fluorophenyl) carbamate (1.1-b) (47 g, 223 mmol, 98.90% yield) as colorless oil. [1123] 1H NMR (DMSO-d6, 400MHz) δ8.98 (s, 1H), 7.68-7.60 (m, 1H), 7.27-7.10 (m, 3H), 1.50 (s, 9H)

98.90%	In tetrahydrofuran; at 25 - 80℃; for 12h;	To a solution of 2-fluoroaniline (1.1-a) (25 g, 225 mmol, 1.0 equiv) in THF (300 mL) was added Boc2O (73.6 g, 337 mmol, 77.5 mL, 1.5 equiv) at 25C, and then stirred at 80C for 12 h. The reaction mixture was concentrated under reduced pressure to give tert-butyl N-(2-fluorophenyl) carbamate (1.1-b) (47 g, 223 mmol, 98.90% yield) as colorless oil. [1123] 1H NMR (DMSO-d6, 400MHz) δ8.98 (s, 1H), 7.68-7.60 (m, 1H), 7.27-7.10 (m, 3H), 1.50 (s, 9H)
97.1%	In tetrahydrofuran; for 48h;Reflux;	o-fluoroaniline111g (1.0mol) and Boc anhydride 327g (1.5mol) were stirred and refluxed in 2200ml of dry tetrahydrofuran for 48h, and the end point of the reaction was identified by thin layer (developing agent: dichloromethane-n-pentane = 1:4). After room temperature, filtration, the filtrate was concentrated to dryness, and the residue was added 1500 ml of petroleum ether, stirred vigorously for 30 min, and allowed to stand, and the supernatant was decanted.The residue was concentrated to dryness to give 205 g of yd.Yield 97.1%
96%	In tetrahydrofuran;Heating / reflux;	To a solution of di-tert-butyldicarbonate (90.4 g, 414 mmol) in tetrahydrofuran (414 mL) was added 2-fluorobenzenamine (40.0 mL, 414 mmol). The reaction was heated at reflux overnight. The reaction was cooled, concentrated, dissolved in pentane, washed, in order, with 1 N potassium bisulfate (2×), water, 20% potassium hydroxide, and brine, and then dried over magnesium sulfate and concentrated to give a light brown oil which was dried under high vacuum to give 83.7 g (96%) as a light brown oil which was used without further purification. 1H-NMR (CDCl3, 500 MHz) δ 1.52 (s, 9H), 6.68 (bs, 1H), 6.85-7.20 (m, 3H), 8.07 (dd, J=8.1, 8.1 Hz, 1H). Mass spec.: 234.18 (MNa)+.
	In tetrahydrofuran; n-Pentane;	tert-Butyl 2-fluorophenylcarbamate To a solution of di-tert-butyldicarbonate (45.2 g, 207 mmol, 1.0 equiv.) in tetrahydrofuran (210 mL) at room temperature was added 2-fluoroaniline (20.0 mL, 207 mmol). The reaction was heated to reflux and held there for 6h. It was cooled, concentrated, dissolved in pentane, washed with 5% citric acid, then 1 M potassium bisulfate (2*), then water, then 20% potassium hydroxide, then brine, dried over magnesium sulfate, and concentrated to give 48.0 g (quant.) as an amber oil which was used without purification. 1H-NMR (CDCl3, 500 MHz) δ 1.52 (s, 9H), 6.68 (bs, 1H), 6.85-7.20 (m, 3H), 8.07 (dd, J=8.1, 8.1, 1H). Mass spec.: 234.18 (MNa)+.
450 mg	In tetrahydrofuran; at 120℃; for 6h;Microwave irradiation;	Aniline 7: Step i: To a solution of 2-fluoroaniline (333 mg, 3.0 mmol) in THF (Volume: 2 ml) was added di-tert-butyl dicarbonate (655 mg, 3.0 ml). The mixture was heated to 120 C under microwave irradiation for 6 hours, cooled and concentrated. The crude product was purified by ISCO affording desired product as an oil (450 mg).
		To a solution of 2-fluoroaniline (1.0 eq.) in tetrahydrofuran (0.2 M) at 0 C. under N2 atmosphere was added dropwise 1M NaHMDS (2.5 eq.). The reaction was stirred for 15 minutes at 0 C., and a solution of di-tert-butyl dicarbonate in tetrahydrofuran was added. The reaction was warmed to room temperature overnight. The solvent was evaporated, and the resulting residue was quenched with 0.1N HCl aqueous solution. The aqueous suspension was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-5% ethyl acetate in hexane to give product as light yellow oil.
		To a solution of 2-fluoroaniline ( 1.0 eq ) in tetrahydrofuran (0.2 M) at O0C under N2 atmosphere was added dropwise IM NaHMDS (2.5 eq.) The reaction was stirred for 15 minutes at O0C, and a solution of di-teτt-butyl dicarbonate in tetrahydrofuran was added. The reaction was warmed to room temperature overnight. The solvent was evaporated, and the resulting residue was quenched with 0.1N HCl aqueous solution. The aqueous suspension was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-5% ethyl acetate in hexane to give product as light <n="171"/>yellow oil.

References: [1]Patent: WO2005/56550,2005,A2 .Location in patent: Page/Page column 35.
[2]Patent: WO2021/72330,2021,A1 .Location in patent: Page/Page column 228; 237.
[3]Patent: WO2022/6340,2022,A1 .Location in patent: Paragraph 1122-1123.
[4]Patent: WO2022/6340,2022,A1 .Location in patent: Paragraph 1122-1123.
[5]Patent: CN104130212,2016,B .Location in patent: Paragraph 0042-0046; 0060-0062.
[6]Patent: US2005/215576,2005,A1 .Location in patent: Page/Page column 46.
[7]Angewandte Chemie - International Edition,2008,vol. 47,p. 888 - 890.
[8]Tetrahedron Letters,2006,vol. 47,p. 1087 - 1091.
[9]Journal of Fluorine Chemistry,2008,vol. 129,p. 97 - 107.
[10]European Journal of Organic Chemistry,2006,p. 2956 - 2969.
[11]Journal of Organic Chemistry,2009,vol. 74,p. 1673 - 1678.
[12]Journal of Medicinal Chemistry,2004,vol. 47,p. 2075 - 2088.
[13]Tetrahedron Letters,2005,vol. 46,p. 767 - 770.
[14]Patent: US2004/204397,2004,A1 .
[15]Journal of Medicinal Chemistry,2008,vol. 51,p. 4858 - 4861.
[16]Journal of the American Chemical Society,2016,vol. 138,p. 9269 - 9276.
[17]Patent: WO2016/106331,2016,A1 .Location in patent: Paragraph 0225.
[18]Patent: US9408907,2016,B2 .Location in patent: Page/Page column 62; 63.
[19]Patent: WO2009/111337,2009,A1 .Location in patent: Page/Page column 168-169.

8
[ 124-38-9 ]
[ 98968-72-0 ]
[ 141940-30-9 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2075 - 2088.

9
[ 98968-72-0 ]
[ 33513-42-7 ]
[ 844891-30-1 ]

Yield	Reaction Conditions	Operation in experiment
100%		tert-Butyl 2-fluorophenylcarbamate (42.7 g, 202 mmol) was concentrated from toluene in vacuo (3×) to remove any traces of water. The resulting residue was dissolved in tetrahydrofuran (600 mL), and cooled to -78 C. To this was added tert-butyllithium (1.7 M in pentane, 285 mL, 485 mmol) in dropwise fashion. After addition was complete, the reaction was stirred at -78 C. for 30 minutes. The solution was allowed to gradually warm to -20 C. before re-cooling to -78 C. To this was added dimethylformamide (46.9 mL, 606 mmol). The reaction was allowed to gradually warm to room temperature overnight. The reaction was poured into a separatory funnel containing diethyl ether and water. The organics were washed with water (3×) and concentrated. The combined aqueous washes were neutralized with 1 M potassium bisulfate and extracted with diethyl ether. The ethereal layers were combined with the other organics, washed with water, then brine, dried over magnesium sulfate, and concentrated to give 48.1 g (100%) as a yellow oil which was used without further purification. 1H-NMR (CDCl3, 500 MHz) δ 1.50 (s, 9H), 7.27 (m, 1H), 7.35 (m, 1H), 7.56 (d, J=7.6 Hz, 1H), 7.85 (bs, 1H), 9.99 (d, J=1.2 Hz, 1H). Mass spec.: 262.16 (MNa)+.

References: [1]Patent: US2005/215576,2005,A1 .Location in patent: Page/Page column 46.
[2]European Journal of Organic Chemistry,2006,p. 2956 - 2969.
[3]Tetrahedron Letters,2005,vol. 46,p. 767 - 770.
[4]Tetrahedron Letters,2005,vol. 46,p. 3493 - 3496.
[5]Journal of Medicinal Chemistry,2008,vol. 51,p. 4858 - 4861.

10
[ 98968-72-0 ]
[ 908600-92-0 ]

Yield	Reaction Conditions	Operation in experiment
65%		Step A: (2-fluoro-6-iodo-phenyl)-carbamic acid terf-butyl esterTo a cooled (-78 C) solution of (2-fluoro-phenyl)-carbamic acid ferf-butyl ester (38.0 g, 180 mmol) in THF (700 mL) under nitrogen was added ferf-butyllithium (1.7 M, 240 mL, 408 mmol). The mixture was stirred for 1 h at -78 C and then a solution of iodine (60.8 g, 240 mmol) in THF (150 mL) was added slowly. The reaction mixture was stirred for further 1 h. Saturated aqueous ammonium chloride (100 mL) was added slowly and the mixture was warmed to RT. The layers were separated and the aqueous layer was extracted with ethyl acetate (2 x 100 mL). The combined organic fractions were washed with brine (200 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography (5% ethyl acetate:hexanes) to afford 39.1 g (65%) of the title compound as a while solid. 1 H NMR (300 MHz, CDCI3): δ 1 .50 (s, 9H), 5.98 (br. s, 1 H), 6.92 - 6.99 (m, 1 H), 7.08 - 7.15 (m, 1 H), 7.62 (dt, J=7.8, 1.2 Hz, 1 H).

References: [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 888 - 890.
[2]European Journal of Organic Chemistry,2006,p. 2956 - 2969.
[3]Patent: WO2011/100502,2011,A1 .Location in patent: Page/Page column 53.

11
[ 98968-72-0 ]
7-fluoro-1H-indole-6-carboxylic acid [ No CAS ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.
[2]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

12
[ 98968-72-0 ]
[ 908600-90-8 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

13
[ 98968-72-0 ]
[ 908600-88-4 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.
[2]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

14
[ 98968-72-0 ]
[ 908600-89-5 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

15
[ 98968-72-0 ]
[ 908600-84-0 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.
[2]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

16
[ 98968-72-0 ]
[ 387-44-0 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2956 - 2969.
[2]European Journal of Organic Chemistry,2006,p. 2956 - 2969.

17
[ 98968-72-0 ]
[ 854538-98-0 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 3493 - 3496.
[2]Tetrahedron Letters,2005,vol. 46,p. 3493 - 3496.

18
[ 98968-72-0 ]
[ 854539-00-7 ]