[ CAS No. 1035235-27-8 ]

Name: tert-Butyl 4-bromoisoindoline-2-carboxylate
Brand: Ambeed
SKU: A152606
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Quality Control of [ 1035235-27-8 ]

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COA GC NMR CNMR HPLC/UPLC LC-MS SDS

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SDS

Product Details of [ 1035235-27-8 ]

CAS No. :	1035235-27-8	MDL No. :	MFCD10700130
Formula :	C₁₃H₁₆BrNO₂	Boiling Point :	363.2°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	298.18	Pubchem ID :	49853504
Synonyms :

Computed Properties of [ 1035235-27-8 ]

TPSA :Topological Polar Surface Area	29.5	H-Bond Acceptor Count :	2
XLogP3 :	2.9	H-Bond Donor Count :	0
SP3 :	0.46	Rotatable Bond Count :	2

Safety of [ 1035235-27-8 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P280-P305 P351 P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1035235-27-8 ]

Upstream synthesis route of [ 1035235-27-8 ]
Downstream synthetic route of [ 1035235-27-8 ]

[ 1035235-27-8 ] Synthesis Path-Upstream 1~3

1
[ 923590-95-8 ]
[ 24424-99-5 ]
[ 1035235-27-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In tetrahydrofuran at 10 - 20℃; for 12.00 h;	Step e. TEA (126 ml, 903 mmol) was added drop-wise over 5 min to a stirred suspension of 4- bromoisoindoline HQ (100 g, 430 mmol) in THF (700 ml) and the mixture was cooled to 10°C. The cooled mixture was then treated with a solution of di-tert-butyl dicarbonate (122 g, 559 mmol) in THF (300 ml) over 15 min whilst maintaining the temperature below 20°C, and the resulting mixture was stirred at rt for 12 h. The reaction was concentrated under vacuum to give an oil, which was partitioned between EtOAc (600 ml) and water (600 ml). The aqueous phase was collected and extracted with EtOAc (2 χ 500 ml), and the combined organic extracts were washed with brine, dried over Na2S04, filtered and evaporated to dryness under vacuum to give the crude product as a solid (161 g). The crude solid was slurried in hexane (150 ml), filtered and the resulting solid washed with hexane (60 ml) before being dried under vacuum at rt to give the desired product as a solid (95.7 g, 75percent). LCMS (Method R): rt 3.02 min, m/z 242 (-tBu)/198(-Boc) [M+H]+; NMR (400 MHz, DMSO-d6) δ ppm 7.51-7.46 (dd, J = 7.8, 0.6 Hz, 1H), 7.38-730 (m, 1H), 7.29-7.21 (m, 1H), 4.73- 4.63 (d, 2H), 4.56-4.47 (d, 2H), 1.50-1.42 (d, 9H).

Reference： [1] Patent: WO2017/158388, 2017, A1. Location in patent: Page/Page column 55; 214
[2] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7576 - 7582

2
[ 24424-99-5 ]
[ 1035235-27-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 18.00 h;	A solution of 4-bromoisoindoline hydrochloride (1.40 g, 5.97 mmol) in DMF (30 mL) was treated with triethylamine (2.50 mL, 17.9 mmol) and di-tert-butyl dicarbonate (2.08 mL, 8.95 mmol), and the mixture was stirred at room temperature for 18 h. Themixture was diluted with EtOAc (65 mL) and washed three times with saturated aqueousNaHCO3. The organic phase was dried and concentrated. The residue was subjected tocolumn chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-3 0percent), to provide tert-butyl 4-bromoisoindoline-2-carboxylate as a white solid (1.70 g,91percent yield).

Reference： [1] Patent: WO2016/65236, 2016, A1. Location in patent: Page/Page column 118

3
[ 127168-81-4 ]
[ 24424-99-5 ]
[ 1035235-27-8 ]

Reference： [1] Patent: US2008/171754, 2008, A1. Location in patent: Page/Page column 104

[ 1035235-27-8 ] Synthesis Path-Downstream 1~10

1
[ 1035235-27-8 ]
7-(isoindolin-4-yl)-4-methylquinolin-2-amine dihydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 4528 - 4554

2
[ 1035235-27-8 ]
C₁₈H₁₇N₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 4528 - 4554

3
[ 1035235-27-8 ]
C₁₂H₁₁BF₃N₂O^(1-)*K⁽¹⁺⁾ [ No CAS ]
C₂₃H₂₅N₃O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 4528 - 4554

4
[ 64-17-5 ]
[ 1035235-27-8 ]
[ 124-38-9 ]
2-(tert-butyl) 4-ethyl isoindoline-2,4-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; at 120℃; under 45603.1 Torr;	Carbon dioxide (g, 60 atm) was introduced into a lOO-mL pressure tank reactor containing a solution of tert-butyl 4-bromo-2,3-dihydro-lH-isoindole-2-carboxylate (2.00 g, 6.71 mmol), triethylamine (2.80 mL, 20.1 mmol), and [l,l?-bis(diphenylphosphino)ferrocene]- dichloropalladium (II), complex with dichloromethane (820 mg, 1.12 mmol) in ethanol (50 mL). The resulting mixture stirred overnight at 120 C. The reaction was concentrated under vacuum and then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3x50 mL of ethyl acetate, washed with 100 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 : 10)) to afford 2-(tert-butyl) 4-ethyl isoindoline-2,4-dicarboxylate (1.67 g, 85%) as an off-white solid. MS: (ESI, m/z): 292[M+H]+

Reference： [1]Patent: WO2019/204550,2019,A1.Location in patent: Paragraph 00131

5
[ 1035235-27-8 ]
2,6-bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine [ No CAS ]
4-(2,6-bis(benzyloxy)pyridin-3-yl)-1,3-dihydroisoindole-2-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.9%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water;Reflux;	To a stirred solution of tert-butyl 5-bromoisoindoline-2-carboxylate (32-1) (300 mg, 1.00 mmol) in dioxane and water (2.5 ml), was added 2,6-bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)pyridine (25-1) (459 mg, 1.10 mmol) and potassium phosphate (636 mg, 3.00 mmol) at room temperature. The reaction mixture was purged with argon for 5 minutes followed by addition of Pd(dppf)Cl2-DCM (40.8 mg, 50.0 mumol) at room temperature. The reaction mixture was heated to reflux overnight. After completion of reaction (monitored by TLC Rf = 0.4 in 20% ea/ hexane and LCMS), the reaction mixture was filtered and concentrated. The crude residue was purified by flash column (elution with 15 % EtOAc/Hexanes) to afford tert-butyl 5-(2,6- bis(benzyloxy)pyridin-3-yl)isoindoline-2-carboxylate (32-2) (330 mg, 648 mumol, 64.9 %) as a gummy liquid.1H NMR (400 MHz, DMSO-d6) delta 7.65-7.63 (m, 1H), 7.45-7.44 (m, 2H), 7.40-7.38 (m, 2H), 7.36-7.21 (m, 7H), 7.19 (m, 1H), 6.54 (m, 1H), 5.37 (br s, 4H), 4.63-4.60 (m, 2H), 4.43 (br s, 2H), 1.44-1.39 (m, 9H).

Reference： [1]Patent: WO2017/197046,2017,A1.Location in patent: Page/Page column 322; 323

6
[ 1035235-27-8 ]
[ 99769-19-4 ]
tert-butyl 4-(3-(methoxycarbonyl)phenyl)isoindoline-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.33 g	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 80℃; for 24.0h;Inert atmosphere;	Step a. To a stirred solution of <strong>[1035235-27-8]tert-butyl 4-bromoisoindoline-2-carboxylate</strong> (Intermediate 1, 0.35 g, 1.185 mmol) in 1,4-dioxane: water (4: 1; 20 ml) was added Cs2C03 (0.77 g, 2.371 mmol) at rt under nitrogen. The reaction was purged with nitrogen for 15 min. Pd(PPh3)4 (0.14 g, 0.118 mmol) was added to the reaction mixture and purged with nitrogen for 10 min. 3- (Methoxycarbonyl)phenylboronic acid (CAS Number 99769-19-4; available from Combi Blocks) (0.26 g, 1.422 mmol) was added to the reaction mixture. The reaction mixture was heated at 80C for 24 h. The resulting reaction mixture was cooled to rt, poured into water (20 ml) and extracted with EtOAc (3 x 50). The combined organic phase was washed with brine (80 ml). The organic phase was separated, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography (5% EtOAc in hexane) yielding tert-butyl 4-(3- (methoxycarbonyl)phenyl)isoindoline-2-carboxylate (0.33 g, 0.932 mmol). LCMS: Method A, 2.782 min, MS: ES+ 298.4 (M-56); 1H NMR (400 MHz, CDC13) delta ppm 8.04 - 8.11 (m, 2 H), 7.62 (d, J=7.2 Hz, 1H), 7.49 - 7.58 (m, 2 H), 7.40 (t, J=7.2 Hz, 1H), 7.31 - 7.33 (m, 1H), 4.69 - 4.79 (m, 4 H), 3.95 (s, 3 H), 1.53 (s, 9 H).

Reference： [1]Patent: WO2017/158388,2017,A1.Location in patent: Page/Page column 99

7
[ 1035235-27-8 ]
[ 761446-44-0 ]
tert-butyl 4-(1-methyl-1H-pyrazol-4-yl)isoindoline-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.121 g	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 85℃; for 0.5h;	Step a. To a stirred solution of <strong>[1035235-27-8]tert-butyl 4-bromoisoindoline-2-carboxylate</strong> (Intermediate 1, 0.2 g, 0.671 mmol) in l,4-dioxane:water (4.1; 5 ml) were added Cs2C03 (0.44 g, 1.342 mmol) and 1-methyl- lH-pyrazole-4-boronic acid pinacol ester (CAS Number 761446-44-0; available from Combi Blocks) (0.17 g, 0.805 mmol) at rt. The reaction mixture was degassed for 20 min. Pd(PPh3)4 (0.077 g, 0.067 mmol) was added to the reaction mixture at rt. The reaction mixture was heated at 85C for 30 min. The resulting reaction mixture was cooled to rt, diluted with water (100 ml) and extracted with EtOAc (3 x 80 ml). The combined organic phase was separated, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography (30% EtOAc in hexane) yielding tert-butyl 4-(1 -methyl- lH-pyrazol-4-yl)isoindoline-2-carboxylate (0.121 g, 0.404 mmol). LCMS: Method A, 2.335 min, MS: ES+ 300.53; NMR (400 MHz, DMSO-d6) delta ppm 8.03 (d, J=11.2 Hz, 1H), 7.78 (d, J=20.4 Hz, 1H), 7.43 - 7.49 (m, 1H), 7.31 (t, J=7.2 Hz, 1H), 7.19 (t, J=7.6 Hz, 1H), 4.69 (s, 2 H), 4.62 (d, J=11.2 Hz, 2 H), 3.90 (s, 3 H), 1.48 (s, 9 H).

Reference： [1]Patent: WO2017/158388,2017,A1.Location in patent: Page/Page column 70

8
[ 1035235-27-8 ]
2-(2-(tert-butoxycarbonyl)isoindolin-4-yl)-5-cyano-3-fluorobenzoic acid [ No CAS ]

Reference： [1]Patent: WO2017/158388,2017,A1

9
[ 1035235-27-8 ]
tert-butyl 4-(4-cyano-2-fluoro-6-(methoxycarbonyl)phenyl)isoindoline-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/158388,2017,A1

10
[ 1035235-27-8 ]
tert-butyl 4-(2-cyano-5-(2-oxooxazolidin-3-yl)phenyl)isoindoline-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/158388,2017,A1

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H200	Unstable explosive
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H202	Explosive; severe projection hazard
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H222	Extremely flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H316	Causes mild skin irritation
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H332	Harmful if inhaled
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
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H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
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

[ CAS No. 1035235-27-8 ]

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[ 1035235-27-8 ] Synthesis Path-Upstream 1~3

[ 1035235-27-8 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 1035235-27-8 ]

Bromides

Amides

Related Parent Nucleus of [ 1035235-27-8 ]

Indolines

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Related Functional Groups of
[ 1035235-27-8 ]

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[ 1035235-27-8 ]