1035235-26-7|tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate| Ambeed

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Quality Control of [ 1035235-26-7 ] Purity: 98% SDS Specification

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Product Details of [ 1035235-26-7 ]

CAS No. :	1035235-26-7
Formula :	C₂₀H₃₀BNO₄
M.W :	359.27
SMILES Code :	O=C(N1CC2=C(C(B3OC(C)(C)C(C)(C)O3)=CC=C2)CC1)OC(C)(C)C
MDL No. :	MFCD11044677
InChI Key :	RCPDEZAVXYLSOR-UHFFFAOYSA-N
Pubchem ID :	57505885

Safety of [ 1035235-26-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 1035235-26-7 ]

* 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 [ 1035235-26-7 ]

[ 1035235-26-7 ] Synthesis Path-Downstream 1~35

2
[ 215184-78-4 ]
[ 73183-34-3 ]
[ 1035235-26-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 2h;Inert atmosphere;	1 ,1-Dimethylethyl 5-bromo-3,4-dihydro-2(1 H)-isoquinolinecarboxylate (Preparation 53) (2.7g, 8.7 mmol), potassium acetate (2.55g, 26 mmol), [1 ,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (0.63g, 0.87 mmol) and 4.4.4'.4'.5.5.5'.5'-octamethyl-2.2'-bi-1 .3,2-dioxaborolane (4.39g, 17 mmol) were dissolved in 1 ,4-dioxane (40ml), stirred at 800C under nitrogen for 2h and allowed to cool. Water (30ml) was added and the mixture was extracted with ethyl acetate (3x 20ml).The combined organic phases were concentrated in vacuo. Purification of the residue by flash chromatography (ethyl acetate in cyclohexane 15%) gave 1 ,1- dimethylethyl 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,4-dihydro-2(1 H)- isoquinolinecarboxylate as a clear gel (3.25g, 105%). LCMS (Method formate): Retention time 1.51 min, MH+ = 360
89%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In N,N-dimethyl-formamide; at 90℃;Inert atmosphere;	A mixture of tert-butyl 5-bromo-3,4-dihydroisoquinoline-2(lH)-carboxylate (0.500 g, 1.60 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (0.488 g, 1.92 mmol) in DMF (8 mL) was subjected to 3 evacuate-fill cycles with nitrogen. Potassium acetate (0.472 g, 4.80 mmol) and PdCi2(dppf) DCM complex (0.117 g, 0.160 mmol) were added, the mixture was subjected to 2 more evacuate-fill cycles with nitrogen, and heated 90 C overnight under a nitrogen atmosphere. The mixture was cooled to room temperature, diluted with EtOAc, washed sequentially with water, 10% aqueous LiCl and saturated brine, dried and concentrated. The residue was subjected to column chromatography on silica gel, eluting with EtOAc-hexanes, to provide tert-butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(17i)- carboxylate as a white solid (0.514 g, 89% yield). Mass spectrum m/z 360 (M+H)+.
57%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 2h;Inert atmosphere;	1 ,1-Dimethylethyl 5-bromo-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 27) (0.281 g, 0.899 mmol), potassium acetate (0.265 g, 2.70 mmol), [1,f- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (0.066 g, 0.090 mmol) and 4i4i4li4Ii5,5,5',5'-octamethyl-2,2'-bi-1I3,2-dioxaborolane (0.274 g, 1.079 mmol) were dissolved in 1 ,4-dioxane (5 ml) and the resulting mixture was stirred at 800C under nitrogen for 2 hours then cooled to room temperature and diluted with water (15 ml). The aqueous phase was extracted with AcOEt (3 x 10 ml). The combined organic phases were dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (c-Hexane/AcOEt: 15%) gave 1,1- dimethylethyl 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,4-dihydro-2(1 H)- isoquinolinecarboxylate 158 mg, 57%) as a light yellow oil. LCMS: retention time 1.54 min; no mass ion detected.

15.45 g	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos; In 1,4-dioxane; at 120℃; for 48h;Inert atmosphere;	Intermediate E: tert-Butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4- dihydroisoquinoline-2(lH)-carboxylate A solution of tert-butyl 5-bromo-3,4-dihydroisoquinoline-2(lH)-carboxylate (20.00 g, 64.1 mmol), bis(pinacolato)diboron (Boron Molecular, Research Triangle, NC, 24.40 g, 96 mmol), potassium phosphate (40.8 g, 192 mmol), Pd2(dba)3 (Sigma- Aldrich, St. Louis, MO, 0.750 g, 3.20 mmol) and X-Phos (Strem Chemicals Inc., Newburyport, MA, 7.63 g, 16.02 mmol) in 100 mL dioxane was placed under argon and was heated to 120 C for 48 hours. LC/MS showed mostly product, so the reaction mixture was allowed to cool to room temperature, diluted with diethyl ether, and filtered through a plug of diatomaceous earth eluting with diethyl ether. The filtrate was concentrated and the resulting residue was purified by silica gel chromatography (0 to 15% EA in heaxanes) to provide tert-butyl 5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(lH)-carboxylate (15.45 g, 43.0 mmol) as a light yellow oil.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 3h;Inert atmosphere;	To a solution of tert-butyl 5-bromo-3,4- dihydroisoquinoline-2(lH)-carboxylate (4.0 g, 12.8 mmol) in dioxane (60 mL) was added bis(pinacolato)diboron (6.5 g, 25.6 mmol), KOAc (3.76 g, 38.4 mmol) and Pd(dppf)Cl2 (936 mg, 1.15 mmol), and the mixture was stirred at 80C for 3 hours under Ar atmosphere. After cooling down to room temperature, the mixture was filtered through Celite. The filtrate was diluted with water (30 mL), extracted with EtOAc (30 mLx3). The combined organic layers was washed with brine (20 mL), dried over Na2S04 filtered and concentrated. The residue was purified by silica gel chromatography (petroleum ether/ EtOAc = 9/1) to afford tert-butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihydro- isoquinoline-2(lH)-F

References: [1]Patent: WO2010/146105,2010,A1 .Location in patent: Page/Page column 86-87.
[2]Patent: WO2016/65222,2016,A1 .Location in patent: Page/Page column 57.
[3]Patent: WO2010/145202,2010,A1 .Location in patent: Page/Page column 38.
[4]Patent: WO2013/134518,2013,A1 .Location in patent: Page/Page column 39.
[5]Patent: WO2016/44666,2016,A1 .Location in patent: Paragraph 0589; 0591.

3
5-(5-bromo-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]-benzonitrile [ No CAS ]
[ 1035235-26-7 ]
[ 1258440-76-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 120℃; for 0.333333h;Microwave irradiation;	1 ,1-Dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2(1 H)- isoquinolinecarboxylate (Preparation 28) (153 mg, 0.426 mmol), 5-(5-bromo-1,3,4- thiadiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile (Preparation 11) (115 mg, 0.355 mmol), dichlorobis(triphenylphosphine)-palladium (II) (24.90 mg, 0.035 mmol) and Na2CO3 (188 mg, 1.774 mmol) were dissolved in a mixture of DME (3.75 ml) and water (1.25 ml). The mixture was stirred at 12O0C for 20 minutes under microwave irradiation. The mixture was diluted with water (20 ml) and the aqueous phase was extracted with AcOEt (2 x 15 ml). The combined organic phases were dried under Na2Stheta4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (c-Hexane/AcOEt: 0 to 20% gradient) gave 1 ,1- dimethylethyl 5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1 ,3,4-thiadiazol-2-yl)-3,4- dihydro-2(1H)-isoquinolinecarboxylate (105 mg, 62%) as a light yellow oil. LCMS: retention time 1.47 min ; [M+H]+ = 477.01
22%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 120℃; for 0.666667h;Irradiation with microwave;	1 ,1-Dimethylethyl 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,4-dihydro-2(1 H)- isoquinolinecarboxylate (Preparation 54) (1.0g, 2.8 mmol), 5-(5-bromo-1 ,3,4- thiadiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile (Preparation 2) (1.35g, 4.2 mmol), dichlorobis(triphenylphosphine)-palladium (II) (0.2Og, 0.28 mmol) and sodium carbonate (1.48g, 14 mmol) were dissolved in 1 ,2-dimethoxyethane (7.5ml) and water (2.5ml). The resulting mixture was stirred at 1200C for 40min (microwave). Dichlorobis(triphenylphosphine)-palladium (II) (0.2Og, 0.28 mmol) was added and the resulting mixture was stirred at 1200C for 40min (microwave). The mixture was diluted with water (20ml) and extracted with ethyl acetate (3x 15ml). The combined organic phases were dried (Na2SO4) and concentrated in vacuo. Purification of the residue by chromatography (ethyl acetate / cyclohexane, 0 to 30% gradient) gave 1 ,1-dimethylethyl 5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1 ,3,4-thiadiazol-2-yl)- 3,4-dihydro-2(1 H)-isoquinolinecarboxylate (290mg, 22%) as a brown solid. LCMS (Method formate): Retention time 1.43min, MH+ = 477

References: [1]Patent: WO2010/145202,2010,A1 .Location in patent: Page/Page column 39.
[2]Patent: WO2010/146105,2010,A1 .Location in patent: Page/Page column 87-88.

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[ 24424-99-5 ]
[ 1035235-26-7 ]

References: [1]Patent: WO2010/146105,2010,A1 .

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[ 1035235-26-7 ]
[ 1258440-18-4 ]

References: [1]Patent: WO2010/146105,2010,A1 .

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[ 1035235-26-7 ]
[ 1258852-41-3 ]

References: [1]Patent: WO2010/146105,2010,A1 .

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[ 1035235-26-7 ]
[ 1258852-43-5 ]

References: [1]Patent: WO2010/146105,2010,A1 .

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[ 1035235-26-7 ]
[ 1258852-45-7 ]

References: [1]Patent: WO2010/146105,2010,A1 .

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[ 1035235-26-7 ]
[ 1258852-55-9 ]

References: [1]Patent: WO2010/146105,2010,A1 .

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[ 1035235-26-7 ]
[ 1258852-57-1 ]

References: [1]Patent: WO2010/146105,2010,A1 .

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[ 1258856-73-3 ]
[ 1035235-26-7 ]

References: [1]Patent: WO2010/146105,2010,A1 .

12
[ 109-01-3 ]
[ 1035235-26-7 ]
[ 40161-54-4 ]
[ 1454667-72-1 ]

Yield	Reaction Conditions	Operation in experiment
1.68 g		Example 41 : N-(5-Fluorothiazol-2-yl)-5-(2-(4-methylpiperazin-l-yl)-4- (trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide Step 1 : tert-Butyl 5-(2-(4-methylpiperazin-l-yl)-4-(trifluoromethyl)phenyl)-3,4- dihydroisoquinoline-2(lH)-carboxylate A microwave vial charged with 1 -methylpiperazine (2.74 ml, 24.69 mmol) and 1- bromo-2-fluoro-4-(trifluoromethyl)benzene (2.000 g, 8.23 mmol) was heated to 180 C in a microwave reactor for 90 minutes. The reaction mixture was concentrated then transferred to a vial charged with Cl2Pd(AmPhos) (Sigma- Aldrich, St. Louis, MO, 0.291 g, 0.412 mmol), tert-butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(lH)- carboxylate (ASW Medchem, Brunswick, NJ, 2.96 g, 8.23 mmol), and potassium phosphate (8.74 g, 41.2 mmol). 8 mL dioxane and 4 mL water were added, and the reaction mixture was heated to 120 C for 2 hours. After cooling to rt, the reaction mixture was poured into water and extracted with DCM. The organics were concentrated then purified by reverse phase column chromatography [RediSep Gold CI 8 150g, 15 to 100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] yielding tert-butyl 5-(2-(4-methylpiperazin-l-yl)-4- (trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(lH)-carboxylate (1.68g, 3.53 mmol).

References: [1]Patent: WO2013/134518,2013,A1 .Location in patent: Page/Page column 83; 84.

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[ 1035235-26-7 ]
[ 1454667-80-1 ]
[ 1454667-82-3 ]

Yield	Reaction Conditions	Operation in experiment
0.45 g	With potassium phosphate; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); In 1,4-dioxane; water; at 120℃; for 2h;	Step 2: tert-Butyl 5-(2-(5-methyl-lH-imidazol-l-yl)-4-(trifluoromethyl)phenyl)-3,4- dihydroisoquinoline-2(lH)-carboxylate A solution of Cl2Pd(AmPhos) (Sigma-Aldrich, St. Louis, MO, 0.165 g, 0.233 mmol), tert-butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(lH)- carboxylate (ASW Medchem, Brunswick, NJ, 1.254 g, 3.49 mmol), l-(2-bromo-5- (trifluoromethyl)phenyl)-5 -methyl- lH-imidazole (derived above, 0.710 g, 2.327 mmol), and potassium phosphate (1.976 g, 9.31 mmol) in 10 mL dioxane 5 mL water was heated to 120 C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with EtO Ac and the organics were concentrated. The resulting residue was purified by silica gel column chromatography (0 to 100% EtOAc/heptane) yielding tert-butyl 5-(2-(5-methyl-lH- imidazol-l-yl)-4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(lH)-carboxylate (0.450 g, 0.984 mmol).

References: [1]Patent: WO2013/134518,2013,A1 .Location in patent: Page/Page column 86; 87.

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[ 1035235-26-7 ]
[ 481075-58-5 ]
[ 1454667-10-7 ]