954238-61-0|tert-Butyl 2-bromobenzyl(methyl)carbamate| Ambeed

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Quality Control of [ 954238-61-0 ] Purity: 96% SDS Specification

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Product Details of [ 954238-61-0 ]

CAS No. :	954238-61-0
Formula :	C₁₃H₁₈BrNO₂
M.W :	300.19
SMILES Code :	O=C(OC(C)(C)C)N(CC1=CC=CC=C1Br)C
MDL No. :	MFCD09701231
InChI Key :	MDLGVFLVTMLPLA-UHFFFAOYSA-N
Pubchem ID :	63789726

Safety of [ 954238-61-0 ]

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

Application In Synthesis of [ 954238-61-0 ]

* 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 [ 954238-61-0 ]

[ 954238-61-0 ] Synthesis Path-Downstream 1~35

1
[ 954238-61-0 ]
[ 17336-68-4 ]
[ 1207202-01-4 ]

References: [1]Chemistry - A European Journal,2009,vol. 15,p. 13291-13294+13273.

2
[ 24424-99-5 ]
[ 698-19-1 ]
[ 954238-61-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	In tetrahydrofuran; at 20℃; for 16h;	Preparation of ferf-butyl 2-bromobenzyl(methyl)carbamate (59). 58 59 A solution of compound 58 (2.0 g, 10.0 mmol) and Boc20 (2.29 g, 10.5 mmol) in THF (40 mL) was stirred at RT for 16 hours. The mixture was then concentrated in vacuo. The crude product was purified by flash column chromatography over silica gel, which was eluted with 10% EtOAc in heptanes, and yielded compound 59 as a colorless oil (2.8 g, 95% yield). 1H NMR (400 MHz, CDCI3) δ 7.54 (d, 1 H), 7.30 (t, 1 H), 7.13 (m, 2 H), 4.53 (br d, 2 H), 2.87 (br s, 3 H), 1.46 (br d, 9 H).
76.9%	In tetrahydrofuran; at 25℃; for 1h;	[0178] Step A: To a mixture of N-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq .) in THF (R.0 mL) was added B0C2O (R80 g, 35.7 mmol, 8.21 mL, 1,10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (S1O2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert-butyl (2-bromobenzyl)(methyl)carbamate (R50 g, 25.0 mmol, 76.9% yield) as a colorless oil. [0179] NMR (400 MHz, CDCb) d 7.55 (br d , J= 8.0 Hz, 1H), 7.34 -7.28 (m, 1H), 7.22-7.08 (m, 2H), 4.61-4.42 (m, 2H), 2.94 -2.78 (m, 3H), 1.60 -1.33 (m, 9H).
76.9%	In tetrahydrofuran; at 25℃; for 1h;	To a mixture of l-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq.) in THF (70.0 mL) was added B0C2O (7.80 g, 35.7 mmol, 8.21 mL, 1.10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert- butyl (2- bromobenzyl)(methyl)carbamate (7.50 g, 25.0 mmol, 76.9% yield) as a colorless oil. (0179) [0165] 1H NMR (400 MHz, CDCb) d 7.55 (br d, J= 8.0 Hz, 1H), 7.34 - 7.28 (m, 1H), 7.22 - (0180) 7.08 (m, 2H), 4.61 - 4.42 (m, 2H), 2.94 - 2.78 (m, 3H), 1.60 - 1.33 (m, 9H).

76.9%	In tetrahydrofuran; at 25℃; for 1h;	To a mixture of 1-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq.) in THF (70.0 mL) was added Boc2O (7.80 g, 35.7 mmol, 8.21 mL, 1.10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert-butyl (2-bromobenzyl)(methyl)carbamate (7.50 g, 25.0 mmol, 76.9% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.55 (br d, J = 8.0 Hz, 1H), 7.34 - 7.28 (m, 1H), 7.22 -7.08 (m, 2H), 4.61 - 4.42 (m, 2H), 2.94 - 2.78 (m, 3H), 1.60 - 1.33 (m, 9H).
76.9%	In tetrahydrofuran; at 25℃; for 1h;	To a mixture of 1-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq.) in THF (70.0 mL) was added Boc2O (7.80 g, 35.7 mmol, 8.21 mL, 1.10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert-butyl (2-bromobenzyl)(methyl)carbamate (7.50 g, 25.0 mmol, 76.9% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.55 (br d, J = 8.0 Hz, 1H), 7.34 - 7.28 (m, 1H), 7.22 -7.08 (m, 2H), 4.61 - 4.42 (m, 2H), 2.94 - 2.78 (m, 3H), 1.60 - 1.33 (m, 9H).

References: [1]Patent: WO2013/132376,2013,A1 .Location in patent: Page/Page column 167.
[2]Patent: WO2021/127429,2021,A1 .Location in patent: Paragraph 0178-0179.
[3]Patent: WO2021/173524,2021,A1 .Location in patent: Paragraph 0164-0165.
[4]Patent: WO2022/26465,2022,A1 .Location in patent: Paragraph 0159-0161.
[5]Patent: WO2022/26465,2022,A1 .Location in patent: Paragraph 0159-0161.

3
[ 954238-61-0 ]
methyl 2-(((2-amino-5-bromopyridin-3-yl)oxy)methyl)-4-fluorobenzoate [ No CAS ]
C₂₆H₂₈FN₃O₅ [ No CAS ]

References: [1]Patent: WO2013/132376,2013,A1 .

4
[ 954238-61-0 ]
methyl 2-(((2-amino-5-bromopyridin-3-yl)oxy)methyl)-4-fluorobenzoate [ No CAS ]
[ 201733-56-4 ]
C₂₇H₃₀FN₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%		Step 1 : To a degassed solution of compound 35 (350 mg, 0.99 mmol), bis(neopentylglycolato)diboron (289 mg, 1.3 mmol) and KOAc (339 mg, 3.4 mmol) in DMSO (10 mL) was added Pd(dppf)CI2 (80 mg, 0.1 mmol). The resulting mixture was stirred at 75 C for 1 h. LCMS analysis indicated that the boronic acid intermediate was formed. After cooling to RT, compound 59 (31 1 mg, 1.03 mmol) and NaHC03 (aq) (1 M solution, 3.0 mL, 3.0 mmol) and dioxane (10 mL) were added. The mixture was degassed, followed by the addition of Pd(dppf)CI2 (80 mg, 0.1 mmol). The resulting mixture was stirred at 80 C for 2 hours and concentrated in vacuo, ethyl acetate (100 mL) and water (150 mL) were added and then partitioned. The aqueous was extracted with EtOAc (2 x 100 mL), and the combined organic layers were washed with brine (400 mL), dried over MgS04, and then concentrated in vacuo. Purification by flash column chromatography over silica gel, which was eluted with 1 % MeOH and 10% heptane in DCM, gave compound 355 as a yellow solid (260 mg, 53% yield). 1 H NMR (400 MHz, CDCI3) δ 8.06 (dd, 1 H), 7.66 (s, 1 H), 7.16 - 7.30 (m, 5 H), 7.05 (ddd, 1 H), 6.86 (d, 1 H), 5.53 (s, 2 H), 4.80 (br s, 2H), 4.33 (br s, 2 H), 3.96 (s, 3 H), 2.63 (br d, 3 H), 1.42 (br d, 9 H). LCMS ES m/z 440 [M-'Bu]+.

References: [1]Patent: WO2013/132376,2013,A1 .Location in patent: Page/Page column 268-269.

5
[ 954238-61-0 ]
[ 73183-34-3 ]
tert-butyl N-methyl-N-[[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.8%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere;	[0180] Step B: A mixture of <strong>[954238-61-0]tert-butyl (2-bromobenzyl)(methyl)carbamate</strong> (R00 g, 23.3 mmol, 1.00 eq.), bis(pinacolato)diboron (8.88 g, 35.0 mmol, 1.50 eq.), Pd(dppf)Ch (1.71 g, 2.33 mmol, 0.10 eq.) and potassium acetate (5.72 g, 58.3 mmol, 2.50 eq) in dioxane (80.0 mL) was degassed and purged with nitrogen for 3 times, and then the mixture was stirred at 110 C for 12 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure to give a residue, and the residue was purified by column chromatography (S1O2, petroleum ether/ethyl acetate = 1/0 to 10/1) to give tert-butyl methyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate (8.00 g, 23.0 mmol, 98.8% yield) as a colorless oil. [0181] NMR (400 MHz, CDCb) d 7.82 (br d, / = 7.2 Hz, 1H), 7.48 -7.37 (m, 1H), 7.27-7.21 (m, 2H), 4.85-4.63 (m, 2H), 2.92-2.73 (m 3H), 1.54 -1.41 (m, 9H), 1.35 (s, 12H).
98.8%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere;	A mixture of <strong>[954238-61-0]tert-butyl (2-bromobenzyl)(methyl)carbamate</strong> (7.00 g, 23.3 mmol, 1.00 eq.), bis(pinacolato)diboron (8.88 g, 35.0 mmol, 1.50 eq.), Pd(dppf)C12 (1.71 g, 2.33 mmol, 0.10 eq.) and potassium acetate (5.72 g, 58.3 mmol, 2.50 eq.) in dioxane (80.0 mL) was degassed and purged with nitrogen for 3 times, and then the mixture was stirred at 110 C for 12 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure to give a residue, and the residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 1/0 to 10/1) to give tert-butyl methyl(2-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)benzyl)carbamate (8.00 g, 23.0 mmol, 98.8% yield) as a colorless oil. (0182) [0167] 1H NMR (400 MHz, CDCb) d 7.82 (br d , J= 7.2 Hz, 1H), 7.48 - 7.37 (m, 1H), 7.27 - (0183) 7.21 (m, 2H), 4.85 - 4.63 (m, 2H), 2.92 - 2.73 (m 3H), 1.54 - 1.41 (m, 9H), 1.35 (s, 12H).
98.8%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere;	A mixture of <strong>[954238-61-0]tert-butyl (2-bromobenzyl)(methyl)carbamate</strong> (7.00 g, 23.3 mmol, 1.00 eq.), bis(pinacolato)diboron (8.88 g, 35.0 mmol, 1.50 eq.), Pd(dppf)Cl2(1.71 g, 2.33 mmol, 0.10 eq.) and potassium acetate (5.72 g, 58.3 mmol, 2.50 eq.) in dioxane (80.0 mL) was degassed and purged with nitrogen for 3 times, and then the mixture was stirred at 110 C for 12 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure to give a residue, and the residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 1/0 to 10/1) to give tert-butyl methyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate (8.00 g, 23.0 mmol, 98.8% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.82 (br d, J = 7.2 Hz, 1H), 7.48 - 7.37 (m, 1H), 7.27 -7.21 (m, 2H), 4.85 - 4.63 (m, 2H), 2.92 - 2.73 (m 3H), 1.54 - 1.41 (m, 9H), 1.35 (s, 12H).

98.8%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere;	A mixture of <strong>[954238-61-0]tert-butyl (2-bromobenzyl)(methyl)carbamate</strong> (7.00 g, 23.3 mmol, 1.00 eq.), bis(pinacolato)diboron (8.88 g, 35.0 mmol, 1.50 eq.), Pd(dppf)Cl2(1.71 g, 2.33 mmol, 0.10 eq.) and potassium acetate (5.72 g, 58.3 mmol, 2.50 eq.) in dioxane (80.0 mL) was degassed and purged with nitrogen for 3 times, and then the mixture was stirred at 110 C for 12 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure to give a residue, and the residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 1/0 to 10/1) to give tert-butyl methyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate (8.00 g, 23.0 mmol, 98.8% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.82 (br d, J = 7.2 Hz, 1H), 7.48 - 7.37 (m, 1H), 7.27 -7.21 (m, 2H), 4.85 - 4.63 (m, 2H), 2.92 - 2.73 (m 3H), 1.54 - 1.41 (m, 9H), 1.35 (s, 12H).
95%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 3h;Inert atmosphere;	To a stirred mixture of tor-butyl (2-bromobenzyl)(methyl)carbamate (57) (1.00 g, 3.33 mmol) and bis(pinacolato)diboron (58) (1.30 g, 5.12 mmol) in 1,4-dioxane (10 mL) were added potassium acetate(0.98 g, 9.99 mmol) and [l'l-bis(diphenylphosphino)ferrocene]dichloro palladium(II) (0.12 g, 0.16 mmol) at room temperature under a nitrogen atmosphere. The resulting mixture was purged with nitrogen consecutively three times and was stirred for 3 h at 100C under a nitrogen atmosphere. The resulting mixture was cooled down to room temperature and filtered. The filtered cake was washed with DCM (3 x1O mL). The combined filtrates were concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (9% of ethyl acetate in petroleum ether) to afford tert-butyl methyl(2- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzyl)carbamate (59) as a light yellow oil.[00426] Yield 1.10 g (95%).1H NMR (400 MHz, CDCl3) δ 7.83 (dd, J=1.6, 7.6 Hz, 1H), 7.44 (dt, J=1.6, 7.6 Hz, 1H), 7.28 - 7.22 (m, 2H), 4.79 (s, 2H), 2.85 (s, 3H), 1.36 (s, 12H), 1.28 (s, 9H). m/z: [ESI+] 348 (M+H)+.

References: [1]Patent: WO2021/127429,2021,A1 .Location in patent: Paragraph 0180-0181.
[2]Patent: WO2021/173524,2021,A1 .Location in patent: Paragraph 0166-0167.
[3]Patent: WO2022/26465,2022,A1 .Location in patent: Paragraph 0162-0163.
[4]Patent: WO2022/26465,2022,A1 .Location in patent: Paragraph 0162-0163.
[5]Patent: WO2021/154902,2021,A1 .Location in patent: Paragraph 00425-00426.

6
[ 954238-61-0 ]
tert-butyl (2-(5-((R)-N-(((R)-tert-butylsulfinyl)amino)ethyl)thiophen-3-yl)benzyl)(methyl)carbamate [ No CAS ]

References: [1]Patent: WO2021/127429,2021,A1 .
[2]Patent: WO2021/173524,2021,A1 .
[3]Patent: WO2022/26465,2022,A1 .

7
[ 954238-61-0 ]
tert-butyl (R)-(2-(5-(1-aminoethyl)thiophen-3-yl)benzyl)(methyl)carbamate [ No CAS ]

References: [1]Patent: WO2021/127429,2021,A1 .
[2]Patent: WO2021/173524,2021,A1 .
[3]Patent: WO2022/26465,2022,A1 .

8
[ 954238-61-0 ]
tert-butyl (2-(5-((S)-1-(((R)-tert-butylsulfinyl)amino)ethyl)thiophen-3-yl)benzyl)(methyl)carbamate [ No CAS ]

References: [1]Patent: WO2021/127429,2021,A1 .
[2]Patent: WO2021/173524,2021,A1 .
[3]Patent: WO2022/26465,2022,A1 .

9
[ 954238-61-0 ]
tert-butyl (2-(5-(1-((6,7-dimethoxyphthalazin-1-yl)amino)ethyl)thiophen-3-yl)benzyl)(methyl)carbamate [ No CAS ]