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[ CAS No. 262433-02-3 ]

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Chemical Structure| 262433-02-3
Chemical Structure| 262433-02-3
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Product Details of [ 262433-02-3 ]

CAS No. :262433-02-3 MDL No. :MFCD08458201
Formula : C18H28BNO5 Boiling Point : 416.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :349.23 g/mol Pubchem ID :-
Synonyms :

Safety of [ 262433-02-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 262433-02-3 ]

  • Upstream synthesis route of [ 262433-02-3 ]
  • Downstream synthetic route of [ 262433-02-3 ]

[ 262433-02-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 262433-02-3 ]
  • [ 461699-81-0 ]
YieldReaction ConditionsOperation in experiment
68% With trifluoroacetic acid In dichloromethane at 5 - 20℃; for 2 h; A mixture of Example 175C (45.0 g, 0.129 mole) in dichloromethane (270 mL) was cooled to <5 C. in an ice bath and treated with a 1:1 solution of TFA/dichloromethane (500 mL) while maintaining the reaction temperature below 5 C. The reaction was warmed to ambient temperature and stirred for 2 hours. The solvents were removed by evaporation at a pressure of 30 Torr and a bath temperature of <30 C. The residue was dissolved in dichloromethane (250 mL) and carefully washed with 2.5N sodium hydroxide (300 mL). The organic layer was extracted with brine (100 mL), dried (MgSO4), filtered, and concentrated to provide the desired product (21.7 g, 68percent). 1H NMR (DMSO-d6, 400 MHz) ? 7.05 (d, 1H), 6.98 (d, 1H), 6.59 (d, 1H), 5.13 (s, 2H), 3.75 (s, 3H), 1.25 (s, 12H); reverse phase HPLC (Hypersil HS, 5 ?m, 100 ?, 4.6?250 mm; 25percent-100percent acetonitrile/0.05M ammonium acetate over 10 minutes, 1 mL/min) Rt 11.03 min.
68%
Stage #1: With trifluoroacetic acid In dichloromethane at 5 - 20℃; for 2 h;
Stage #2: With sodium hydroxide In dichloromethane; water
[0590] A mixture of Example 175C (45.0 g, 0.129 mole) in dichloromethane (270 mL) was cooled to <5° C. in an ice bath and treated with a 1:1 solution of TFA/dichloromethane (500 mL) while maintaining the reaction temperature below 5° C. The reaction was warmed to ambient temperature and stirred for 2 hours. The solvents were removed by evaporation at a pressure of 30 Torr and a bath temperature of <30° C. The residue was dissolved in dichloromethane (250 mL) and carefully washed with 2.5N sodium hydroxide (300 mL). The organic layer was extracted with brine (100 mL), dried (MgSO4), filtered, and concentrated to provide the desired product (21.7 g, 68percent). 1H NMR (DMSO-d6, 400 MHz) δ 7.05 (d, 1H), 6.98 (d, 1H), 6.59 (d, 1H), 5.13 (s, 2H), 3.75 (s, 3H), 1.25 (s, 12H); reverse phase HPLC (Hypersil HS, 5 μm, 100 A, 4.6.x.250 mm; 25percent-100percent acetonitrile/0.05M ammonium acetate over 10 minutes, 1 mL/min) Rt 11.03 min.
67.5% With trifluoroacetic acid In dichloromethane A.
2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
A mixture of tert-butyl N-[2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (45.0 g,.129 mol) was dissolved in dichloromethane (270 mL) then the solution was cooled to 5° C. in and ice bath.
A mixture of 20percent trifluoroacetic acid in dichloromethane was added dropwise over the course of one hour while maintaining the temperature of the mixture at <5° C.
The reaction mixture was warmed to ambient temperature and stirred for 2 hours.
The solvents were removed under reduced pressure then the resulting oil was dissolved in dichloromethane (250 mL) and cautiously extracted with 2.5 N aqueous sodium hydroxide (300 mL) then brine (100 mL).
The organic solution was dried over magnesium sulfate, filtered and the fitrate concentrated under reduced pressure to give 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (21.7 g, 67.5percent) as a light brown solid bismaleate: 1H NMR (DMSO-d6, 400 MHz) δ 7.06 (d, 1H), 6.98 (s, 1H), 8.09 (d, 1H), 6.59 (d, 1H), 5.13 (bs, 2H), 3.76 (s, 3H), 1.26 (s, 12H); RP-HPLC (Hypersil HS C18Hypersil HS C18, 5 μm, 100 A, 250*4.6 mm; 25percent-100percent acetonitrile-0.05 M ammonium acetate over 10 min, 1 mL/min) tr 10.85 min.
67.5% With trifluoroacetic acid In dichloromethane A.
2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
A mixture of tert-butyl N-[2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (45.0 g, 0.129 mol) was dissolved in dichloromethane (270 mL) then the solution was cooled to 5° C. in and ice bath.
A mixture of 20percent trifluoroacetic acid in dichloromethane was added dropwise over the course of one hour while maintaining the temperature of the mixture at <5° C.
The reaction mixture was warmed to ambient temperature and stirred for 2 hours.
The solvents were removed under reduced pressure then the resulting oil was dissolved in dichloromethane (250 mL) and cautiously extracted with 2.5 N aqueous sodium hydroxide (300 mL) then brine (100 mL).
The organic solution was dried over magnesium sulfate, filtered and the fitrate concentrated under reduced pressure to give 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (21.7 g, 67.5percent) as a light brown solid bismaleate: 1H NMR (DMSO-d6, 400 MHz) δ 7.06 (d, 1H), 6.98 (s, 1H), 8.09 (d, 1H), 6.59 (d, 1H), 5.13 (bs, 2H), 3.76 (s, 3H), 1.26 (s, 12H); RP-HPLC (Hypersil HS C18 Hypersil HS C18, 5 μm, 100 A, 250*4.6 mm; 25percent-100percent acetonitrile-0.05 M ammonium acetate over 10 min, 1 mL/min) tr 10.85 min.

Reference: [1] Patent: US2005/20619, 2005, A1, . Location in patent: Page 40-41
[2] Patent: US2005/43347, 2005, A1, . Location in patent: Page/Page column 49
[3] Patent: US2002/156081, 2002, A1,
[4] Patent: US6921763, 2005, B2,
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