[ CAS No. 1228014-35-4 ] {[proInfo.proName]}

Name: 1228014-35-4|tert-Butyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate|96%
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Product Details of [ 1228014-35-4 ]

CAS No. :	1228014-35-4	MDL No. :	MFCD20527472
Formula :	C₁₂H₁₃BrN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XIWJCGZCLBMYBC-UHFFFAOYSA-N
M.W :	297.15	Pubchem ID :	58298320
Synonyms :

Safety of [ 1228014-35-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1228014-35-4 ]

* 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.

Upstream synthesis route of [ 1228014-35-4 ]
Downstream synthetic route of [ 1228014-35-4 ]

[ 1228014-35-4 ] Synthesis Path-Upstream 1~1

1
[ 24424-99-5 ]
[ 348640-06-2 ]
[ 1228014-35-4 ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2 h;	j0695j To a solution of 4-bromo-1H-pyrrolo[2,3-bjpyridine (XCI) (5 g, 25.4 mmol, 1 eq.), DMAP (311 mg, 2.55 mmol, 0.1 eq.) and TEA (5.3 mL, 38 mmol, 3 eq.) in DCM (100 mL) was added Boc2O (7.2 mL, 31 mmol, 1.2 eq.) at 0°C. The reaction was warmed to room temperature and stirred for 2 h. Water (100 mL) was added and extracted with DCM (x 2). Removal solvents gave tert-butyl 4-bromo-1H-pyrrolo[2,3-bjpyridine-1-carboxylate (XCII) as a colorless oil (6.95 g, 23.4 mmol, 92.1percent yield). ‘H NMR (CDC13, 400 MHz) ppm 1.60 (s, 9H), 6.50 (d, J=4Hz, 1H), 7.31 (d,J=5.2Hz, 1H), 7.63 (d,J=4Hz, 1H), 8.23 (d,J=5.2Hz, 1H); ESIMS found for C,2H,3BrN2O2 mlz 297.1 (M+H).
92.1%	With dmap; triethylamine In dichloromethane at 0 - 25℃; for 2 h;	To a solution of 4-bromo-lH-pyrrolo[2,3-b]pyridine (LXXIV) (5 g, 25.4 mmol, 1 eq.), DMAP (311 mg, 2.55 mmol, 0.1 eq.) and TEA (5.3 mL, 38 mmol, 3 eq.) in DCM (100 mL) was added B0C2O (7.2 mL, 31 mmol, 1.2 eq.) at 0°C. The reaction was warmed to room temperature and stirred for 2 h. Water (100 mL) was added and extracted with DCM (x 2). Removal solvents gave fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (LXXV) as a colorless oil (6.95 g, 23.4 mmol, 92.1percent yield). NMR (CDCI3, 400 MHz) δ ppm 1.60 (s, 9H), 6.50 (d, J=4Hz, 1H), 7.31 (d, J=5.2Hz, 1H), 7.63 (d, J=4Hz, 1H), 8.23 (d, J=5.2Hz, 1H); ESIMS found for Ci2Hi₃BrN₂02 mlz 297.1 (M+H).
92.1%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2 h;	Step 1 [0676] To a solution of 4-bromo-lH-pyrrolo[2,3-b]pyridine (LXXIV) (5 g, 25.4 mmol, 1 eq.), DMAP (311 mg, 2.55 mmol, 0.1 eq.) and TEA (5.3 mL, 38 mmol, 3 eq.) in DCM (100 mL) was added B0C2O (7.2 mL, 31 mmol, 1.2 eq.) at 0°C. The reaction was warmed to room temperature and stirred for 2 h. Water (100 mL) was added and extracted with DCM (x 2). Removal solvents gave fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (LXXV) as a colorless oil (6.95 g, 23.4 mmol, 92.1percent yield). NMR (CDCI3, 400 MHz) δ ppm 1.60 (s, 9H), 6.50 (d, J=4Hz, 1H), 7.31 (d, J=5.2Hz, 1H), 7.63 (d, J=4Hz, 1H), 8.23 (d, J=5.2Hz, 1H); ESIMS found for Ci2Hi₃BrN₂02 mlz 297.1 (M+H).

92.1%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2 h;	To a solution of 4-bromo-lH-pyrrolo[2,3-b]pyridine (LXXIV) (5 g, 25.4 mmol, 1 eq.), DMAP (311 mg, 2.55 mmol, 0.1 eq.) and TEA (5.3 mL, 38 mmol, 3 eq.) in DCM (100 mL) was added B0C2O (7.2 mL, 31 mmol, 1.2 eq.) at 0°C. The reaction was warmed to room temperature and stirred for 2 h. Water (100 mL) was added and extracted with DCM (x 2). Removal solvents gave fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (LXXV) as a colorless oil (6.95 g, 23.4 mmol, 92.1percent yield). NMR (CDCI3, 400 MHz) δ ppm 1.60 (s, 9H), 6.50 (d, J=4Hz, 1H), 7.31 (d, J=5.2Hz, 1H), 7.63 (d, J=4Hz, 1H), 8.23 (d, J=5.2Hz, 1H); ESIMS found for Ci2Hi₃BrN₂02 mlz 297.1 (M+H).
87%	With triethylamine In tetrahydrofuran at 0 - 70℃;	Scheme 17: Synthesis of tert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yI)-lH- pyrrolo[2,3-b]pyridine-l-carboxylate [77] 75 76 77Step 1Compound [75] (1.0 g, 5.1 mmol) was dissolved in THF (30 ml) and the temperature brought down to 0 °C with an ice bath. To this reaction mixture TEA (1.41 ml, 10.2 mmol), followed by BOC anhydride (1.33 g, 6.2 mmol) was added. A catalytic amount of DMAP (50 mg) was then added. This reaction mixture was then allowed to stirred and refluxed under nitrogen at 70°C for 18 h. TLC and mass spectral analysis confirmed completion of the reaction. The reaction mixture was diluted with ethyl acetate (30 ml) which was washed with water and brine solution. The organic layers were combined, dried using anhydrous Na₂S0₄., filtered, and evaporated to yield [76] as a brown solid (1.3 g, 87percent).ESIMS: 298 (M⁺ +l)
87%	With dmap; triethylamine In tetrahydrofuran at 0 - 70℃; Inert atmosphere	Step 1 Compound [75] ( 1.0 g, 5. 1 mmol) was dissolved in THF (30 ml) and the temperature brought down to 0 °C with an ice bath. To this reaction mixture TEA ( 1.41 ml, 10.2 mmol), followed by BOC anhydride ( 1.33 g, 6.2 mmol) was added. A catalytic amount of DMAP (50 mg) was then added. This reaction mixture was then allowed to stirred and refluxed under nitrogen at 70°C for 18 h. TLC and mass spectral analysis confirmed completion of the reaction. The reaction mixture was diluted with ethyl acetate (30 ml) which was washed with water and brine solution. The organic layers were combined, dried using anhydrous NaiS0₄., filtered, and evaporated to yield [76] as a brown solid ( 1.3 g, 87percent). ESIMS: 298 (M⁺ + 1 )
61%	With triethylamine In dichloromethane at 20℃; for 3 h;	A mixture of 4-bromo-lH-pyrrolo[2,3-δ]pyridine (250 mg, 1.26 mmol), di-te/t-butyl dicarbonate (302 mg, 1.38 mmol), dimethyl-pyridin-4-yl-amine (7.6 mg, 0.06 mmol) and triethylamine (127 mg, 1.26 mmol) in anhydrous methylene chloride (15 rnL) was stirred at room temperature for 3 h. Upon completion of the reaction as indicated by TLC, the volatiles were removed under reduced pressure and the residue was purified by column chromatography on silica gel (9-25 percent ethyl acetate in petroleum ether) to give the desired product (230 mg, 61 percent yield) as an oil. MS (ESI) m/z 242.9 [M-56+l]⁺

Reference： [1] Patent: WO2017/24021, 2017, A1, . Location in patent: Paragraph 0694; 0695
[2] Patent: WO2017/24004, 2017, A1, . Location in patent: Paragraph 0676
[3] Patent: WO2017/23980, 2017, A1, . Location in patent: Paragraph 0676
[4] Patent: WO2017/23996, 2017, A1, . Location in patent: Paragraph 0676
[5] Patent: WO2012/101654, 2012, A2, . Location in patent: Page/Page column 59
[6] Patent: WO2014/16849, 2014, A2, . Location in patent: Page/Page column 115
[7] Patent: WO2010/62571, 2010, A1, . Location in patent: Page/Page column 125-126
[8] Organic and Biomolecular Chemistry, 2011, vol. 9, # 14, p. 5129 - 5136
[9] Patent: WO2017/202742, 2017, A1, . Location in patent: Page/Page column 90; 91

[ 1228014-35-4 ] Synthesis Path-Downstream 1~14

1
[ 24424-99-5 ]
[ 348640-06-2 ]
[ 1228014-35-4 ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	j0695j To a solution of 4-bromo-1H-pyrrolo[2,3-bjpyridine (XCI) (5 g, 25.4 mmol, 1 eq.), DMAP (311 mg, 2.55 mmol, 0.1 eq.) and TEA (5.3 mL, 38 mmol, 3 eq.) in DCM (100 mL) was added Boc2O (7.2 mL, 31 mmol, 1.2 eq.) at 0C. The reaction was warmed to room temperature and stirred for 2 h. Water (100 mL) was added and extracted with DCM (x 2). Removal solvents gave tert-butyl 4-bromo-1H-pyrrolo[2,3-bjpyridine-1-carboxylate (XCII) as a colorless oil (6.95 g, 23.4 mmol, 92.1% yield). ?H NMR (CDC13, 400 MHz) ppm 1.60 (s, 9H), 6.50 (d, J=4Hz, 1H), 7.31 (d,J=5.2Hz, 1H), 7.63 (d,J=4Hz, 1H), 8.23 (d,J=5.2Hz, 1H); ESIMS found for C,2H,3BrN2O2 mlz 297.1 (M+H).
92.1%	With dmap; triethylamine; In dichloromethane; at 0 - 25℃; for 2h;	To a solution of 4-bromo-lH-pyrrolo[2,3-b]pyridine (LXXIV) (5 g, 25.4 mmol, 1 eq.), DMAP (311 mg, 2.55 mmol, 0.1 eq.) and TEA (5.3 mL, 38 mmol, 3 eq.) in DCM (100 mL) was added B0C2O (7.2 mL, 31 mmol, 1.2 eq.) at 0C. The reaction was warmed to room temperature and stirred for 2 h. Water (100 mL) was added and extracted with DCM (x 2). Removal solvents gave fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (LXXV) as a colorless oil (6.95 g, 23.4 mmol, 92.1% yield). NMR (CDCI3, 400 MHz) delta ppm 1.60 (s, 9H), 6.50 (d, J=4Hz, 1H), 7.31 (d, J=5.2Hz, 1H), 7.63 (d, J=4Hz, 1H), 8.23 (d, J=5.2Hz, 1H); ESIMS found for Ci2Hi3BrN202 mlz 297.1 (M+H).
92.1%	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	Step 1 [0676] To a solution of 4-bromo-lH-pyrrolo[2,3-b]pyridine (LXXIV) (5 g, 25.4 mmol, 1 eq.), DMAP (311 mg, 2.55 mmol, 0.1 eq.) and TEA (5.3 mL, 38 mmol, 3 eq.) in DCM (100 mL) was added B0C2O (7.2 mL, 31 mmol, 1.2 eq.) at 0C. The reaction was warmed to room temperature and stirred for 2 h. Water (100 mL) was added and extracted with DCM (x 2). Removal solvents gave fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (LXXV) as a colorless oil (6.95 g, 23.4 mmol, 92.1% yield). NMR (CDCI3, 400 MHz) delta ppm 1.60 (s, 9H), 6.50 (d, J=4Hz, 1H), 7.31 (d, J=5.2Hz, 1H), 7.63 (d, J=4Hz, 1H), 8.23 (d, J=5.2Hz, 1H); ESIMS found for Ci2Hi3BrN202 mlz 297.1 (M+H).

92.1%	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	To a solution of 4-bromo-lH-pyrrolo[2,3-b]pyridine (LXXIV) (5 g, 25.4 mmol, 1 eq.), DMAP (311 mg, 2.55 mmol, 0.1 eq.) and TEA (5.3 mL, 38 mmol, 3 eq.) in DCM (100 mL) was added B0C2O (7.2 mL, 31 mmol, 1.2 eq.) at 0C. The reaction was warmed to room temperature and stirred for 2 h. Water (100 mL) was added and extracted with DCM (x 2). Removal solvents gave fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (LXXV) as a colorless oil (6.95 g, 23.4 mmol, 92.1% yield). NMR (CDCI3, 400 MHz) delta ppm 1.60 (s, 9H), 6.50 (d, J=4Hz, 1H), 7.31 (d, J=5.2Hz, 1H), 7.63 (d, J=4Hz, 1H), 8.23 (d, J=5.2Hz, 1H); ESIMS found for Ci2Hi3BrN202 mlz 297.1 (M+H).
87%	With triethylamine;dmap; In tetrahydrofuran; at 0 - 70℃;	Scheme 17: Synthesis of tert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yI)-lH- pyrrolo[2,3-b]pyridine-l-carboxylate [77] 75 76 77Step 1Compound [75] (1.0 g, 5.1 mmol) was dissolved in THF (30 ml) and the temperature brought down to 0 C with an ice bath. To this reaction mixture TEA (1.41 ml, 10.2 mmol), followed by BOC anhydride (1.33 g, 6.2 mmol) was added. A catalytic amount of DMAP (50 mg) was then added. This reaction mixture was then allowed to stirred and refluxed under nitrogen at 70C for 18 h. TLC and mass spectral analysis confirmed completion of the reaction. The reaction mixture was diluted with ethyl acetate (30 ml) which was washed with water and brine solution. The organic layers were combined, dried using anhydrous Na2S04., filtered, and evaporated to yield [76] as a brown solid (1.3 g, 87%).ESIMS: 298 (M+ +l)
87%	With dmap; triethylamine; In tetrahydrofuran; at 0 - 70℃;Inert atmosphere;	Step 1 Compound [75] ( 1.0 g, 5. 1 mmol) was dissolved in THF (30 ml) and the temperature brought down to 0 C with an ice bath. To this reaction mixture TEA ( 1.41 ml, 10.2 mmol), followed by BOC anhydride ( 1.33 g, 6.2 mmol) was added. A catalytic amount of DMAP (50 mg) was then added. This reaction mixture was then allowed to stirred and refluxed under nitrogen at 70C for 18 h. TLC and mass spectral analysis confirmed completion of the reaction. The reaction mixture was diluted with ethyl acetate (30 ml) which was washed with water and brine solution. The organic layers were combined, dried using anhydrous NaiS04., filtered, and evaporated to yield [76] as a brown solid ( 1.3 g, 87%). ESIMS: 298 (M+ + 1 )
61%	With triethylamine;dmap; In dichloromethane; at 20℃; for 3h;	A mixture of 4-bromo-lH-pyrrolo[2,3-delta]pyridine (250 mg, 1.26 mmol), di-te/t-butyl dicarbonate (302 mg, 1.38 mmol), dimethyl-pyridin-4-yl-amine (7.6 mg, 0.06 mmol) and triethylamine (127 mg, 1.26 mmol) in anhydrous methylene chloride (15 rnL) was stirred at room temperature for 3 h. Upon completion of the reaction as indicated by TLC, the volatiles were removed under reduced pressure and the residue was purified by column chromatography on silica gel (9-25 % ethyl acetate in petroleum ether) to give the desired product (230 mg, 61 % yield) as an oil. MS (ESI) m/z 242.9 [M-56+l]+
	With pyridine; In dichloromethane; at 20℃;Inert atmosphere;	To a solution of pyridine (0.1 mL, 1.236 mmol) in dichloromethane (3 mL) under nitrogen was added 4-bromo-1H-pyrrolo[2,3-b]pyridine (220 mg, 1.117 mmol, commercially available from, for example, Aldrich) and di-tert-butyl dicarbonate (268 mg, 1.228 mmol) . The reaction mixture was stirred at rtovernight. Further pyridine (0.1 mL, 1.236 mmol) and di-tert-butyl dicarbonate (268 mg, 1.228 mmol) were added and the reaction mixture was stirred for 3 hours. Citric acid (1M, 5 mL) was added and the organic phase was separated. The aqueous phase was extracted with further portions of DCM (2 x 5mL). The combined organic phases were dried (hydrophobic frit) then concentrated in vacuo to give tert-butyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (340 mg, 0.973 mmol, 87 % yield,?85% purity).LCMS (2 mm Formic): Rt = 1.25 mi [MH] = 297.1, 299.1

Reference： [1]Patent: WO2017/24021,2017,A1 .Location in patent: Paragraph 0694; 0695
[2]Patent: WO2017/24004,2017,A1 .Location in patent: Paragraph 0676
[3]Patent: WO2017/23980,2017,A1 .Location in patent: Paragraph 0676
[4]Patent: WO2017/23996,2017,A1 .Location in patent: Paragraph 0676
[5]Patent: WO2012/101654,2012,A2 .Location in patent: Page/Page column 59
[6]Patent: WO2014/16849,2014,A2 .Location in patent: Page/Page column 115
[7]Patent: WO2010/62571,2010,A1 .Location in patent: Page/Page column 125-126
[8]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5129 - 5136
[9]Patent: WO2017/202742,2017,A1 .Location in patent: Page/Page column 90; 91

2
[ 1228014-35-4 ]
[ 1228014-32-1 ]
[ 1228014-36-5 ]

Yield	Reaction Conditions	Operation in experiment
35%	With triethylamine;tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine; In 1,4-dioxane; at 95℃;Inert atmosphere;	A mixture of l-(2-(tetrahydro-2Eta- pyran-4-yl)ethyl)-7-(trimethylstannyl)-3 ,4-dihy dropyrazino [2,3 -b]pyrazin-2( 1 H)-one (See Example 15.C) (1 equiv), 4-bomo-pyrrolo[2,3-delta]pyridine-l-carboxylic acid tert-bvXy ester (1 equiv), tris(dibezylideneacetone) palladium (0.13 equiv), tri-o-tolylphosphine (0.25 equiv) and triethylamine (2.8 equiv) in anhydrous dioxane was purged, degassed for 2 min and stirred at 95 0C under nitrogen for 3-4 h. Upon completion of the reaction as indicated by TLC, the volatiles were removed under reduced pressure and the residue was purified by column chromatography to give the desired product in 35 % yield. MS (ESI) m/z 479.7 [M+l]+. tert-Butyl 4-(7-oxo-8-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-5,6,7,8- tetrahydropyrazino[2,3-b]pyrazin-2-yl)-lH-pyrrolo[2,3-b]pyridine-l-carboxylate was stirred in methanolic hydrochloride solution at room temperature. Upon completion of the reaction as indicated by TLC, the solvent was removed under reduced pressure and the residue was purified on silica gel to give the title compound in 63 % yield. 1H NMR (DMSO-J6, 400 MHz) delta (ppm) 11.72 (s, IH), 8.38 (s, IH), 8.25 (d, J=4.8 Hz, IH), 7.79 (s, IH), 7.53-7.51 (m, 2H), 6.97 (q, J=1.6 Hz, IH), 4.23 (s, 2H), 4.14 (t, J=7.6 Hz, 2H), 3.81 (dd, Ji=2.4 Hz, J2=11.2 Hz, 2H), 3.25 (d, J=10.8 Hz, 2H), 1.67 (d, J= 13.2 Hz, 2H), 1.61 (m, 3H), 1.22 (m, 2H); MS(ESI): m/z 379.2 [M+l]+.

Reference： [1]Patent: WO2010/62571,2010,A1 .Location in patent: Page/Page column 122

3
[ 1228014-35-4 ]
[ 1316228-47-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5129 - 5136

4
[ 1228014-35-4 ]
[ 1316228-66-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5129 - 5136

5
[ 1228014-35-4 ]
C₁₄H₁₄N₂O₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5129 - 5136

6
[ 1228014-35-4 ]
[ 1066-54-2 ]
C₁₇H₂₂N₂O₂Si [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5129 - 5136

7
[ 885699-28-5 ]
[ 1228014-35-4 ]
[ 1257384-53-4 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5887 - 5900

8
[ 1228014-35-4 ]
[ 73183-34-3 ]
[ 1391926-50-3 ]

Yield	Reaction Conditions	Operation in experiment
86.4%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 6h;Inert atmosphere;	j0704j A solution of tert-butyl 4-bromo-1H-pyrrolo[2,3-bjpyridine-1-carboxylate (XCII) (2 g, 6.8 mmol, 1.0 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)-1,3,2-dioxaborolane (2.07 g, 8.16 mmol, 1.02 eq), KOAc (1.99 g, 20.4 mmol, 3 eq) in dioxane (25 mL) was degassed (x 3) with a water pump. Pd(dppf)C12 (246 mg, 0.34 mmol, 0.05 eq) was then added quickly in one portion under nitrogen. The reaction was stirred at 90C for 6 h. Water (100 mL) was added and extracted with EtOAc (x 3). Flash chromatography (PE: EtOAc 20:1) gave tert-butyl 4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrrolo[2,3 -bjpyridine- 1- carboxylate (C) as a green oil (2.0 g, 5.82 mmol, 86.4%). ?H NMR (CDC13, 400 MHz) ppm 1.39 (s, 12H), 1.67 (s, 9H), 6.93 (d, J4Hz, 1H), 7.54 (d, J4.8Hz, 1H), 7.65 (d, J4Hz, 1H), 8.51 (d, J4.4Hz, 1H); ESIMS found for C,8H25BN204 mlz 345.1 (M+H).
86.4%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; water; at 90℃; for 6h;Inert atmosphere;	A solution of fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (LXXV) (2 g, 6.8 mmol, l .Q eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)-l,3,2-dioxaborolane (2.07 g, 8.16 mmol, 1.02 eq), KOAc (1.99 g, 20.4 mmol, 3 eq) in dioxane (25 mL) was degassed (x 3) with a water pump. Pd(dppf)Cl2 (246 mg, 0.34 mmol, 0.05 eq) was then added quickly in one portion under nitrogen. The reaction was stirred at 90C for 6 h. Water (100 mL) was added and extracted with EtOAc (x 3). Flash chromatography (PE:EtOAc 20: 1) gave fert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3- b]pyridine-l-carboxylate (LXXXIII) as a green oil (2.0 g, 5.82 mmol, 86.4%). NMR (CDC , 400 MHz) delta ppm 1.39 (s, 12H), 1.67 (s, 9H), 6.93 (d, J=4Hz, 1H), 7.54 (d, J=4.8Hz, 1H), 7.65 (d, J=4Hz, 1H), 8.51 (d, J=4.4Hz, 1H); ESIMS found for C18H25BN2O4 mlz 345.1 (M+H)
86.4%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 6h;Inert atmosphere;	Step 1 [0685] A solution of fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (LXXV) (2 g, 6.8 mmol, l.Q eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)-l,3,2-dioxaborolane (2.07 g, 8.16 mmol, 1.02 eq), KOAc (1.99 g, 20.4 mmol, 3 eq) in dioxane (25 mL) was degassed (x 3) with a water pump. Pd(dppf)Cl2 (246 mg, 0.34 mmol, 0.05 eq) was then added quickly in one portion under nitrogen. The reaction was stirred at 90C for 6 h. Water (100 mL) was added and extracted with EtOAc (x 3). Flash chromatography (PE:EtOAc 20: 1) gave fert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3- b]pyridine-l-carboxylate (LXXXIII) as a green oil (2.0 g, 5.82 mmol, 86.4%). NMR (CDC13, 400 MHz) delta ppm 1.39 (s, 12H), 1.67 (s, 9H), 6.93 (d, J=4Hz, 1H), 7.54 (d, J=4.8Hz, 1H), 7.65 (d, J=4Hz, 1H), 8.51 (d, J=4.4Hz, 1H); ESIMS found for C18H25BN2O4 mlz 345.1 (M+H).

86.4%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 6h;Inert atmosphere;	A solution of fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (LXXV) (2 g, 6.8 mmol, l.Q eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)-l,3,2-dioxaborolane (2.07 g, 8.16 mmol, 1.02 eq), KOAc (1.99 g, 20.4 mmol, 3 eq) in dioxane (25 mL) was degassed (x 3) with a water pump. Pd(dppf)Cl2 (246 mg, 0.34 mmol, 0.05 eq) was then added quickly in one portion under nitrogen. The reaction was stirred at 90C for 6 h. Water (100 mL) was added and extracted with EtOAc (x 3). Flash chromatography (PE:EtOAc 20: 1) gave fert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3- b]pyridine-l-carboxylate (LXXXIII) as a green oil (2.0 g, 5.82 mmol, 86.4%). NMR (CDC13, 400 MHz) delta ppm 1.39 (s, 12H), 1.67 (s, 9H), 6.93 (d, J=4Hz, 1H), 7.54 (d, J=4.8Hz, 1H), 7.65 (d, J=4Hz, 1H), 8.51 (d, J=4.4Hz, 1H); ESIMS found for C18H25BN2O4 mlz 345.1 (M+H).
76%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 100℃; for 18h;Inert atmosphere;	Step 2Compound [76] (1.3 g, 4.37 mmol) was dissolved in 1,4-dioxane (30 ml) in a clean oven- dried two necked RB flask (250ml) and degassed with nitrogen. To this clear solution, bis(pinnacaloto)-diboron (1.3 g, 5.24 mmol) was added, followed by potassium acetate (1.28 g, 813.1 1 mmol) and [1 , l '-bis (diphenylphosphino)ferrocene]palladium(II)chloride with dichloromethane (0.37 g, 0 .437 mmol). The reaction mixture was stirred and heated at 100 C for 18 h , under a nitrogen atmosphere. The reaction was monitored by TLC. Upon completion of the reaction, the reaction mixture was filtered through celite, washed well with ethyl acetate. The filtrate was extracted with ethyl acetate (2 x 30 ml). The organic extracts were combined, washed with brine and dried over Na2S04,filtered and evaporated under vacuum to give [77] as dark brown solid (1.3g), which upon further washing with ether yielded [77] as a brown solid(1.15 g, 76 %).ESIMS: 345 (M+ + l)
76%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 18h;Inert atmosphere;	Step 2 Compound [76] ( 1.3 g, 4.37 mmol ) was dissolved in 1 ,4-dioxane (30 ml) in a clean oven- dried two necked RB flask (250ml) and degassed with nitrogen. To this clear solution, bis(pinna'caloto)-diboron ( 1 .3 g, 5.24 mmol) was added, followed by potassium acetate ( 1 .28 g, 81 3. 1 1 mmol) and [ 1 , l '-bis (diphenylphosphino)fenOcene]palladium(II)chloride with dichloromethane (0.37 g, 0 .437 mmol). The reaction mixture was stirred and heated at 100 completion of the reaction, the reaction mixture was filtered through celite, washed well with ethyl acetate. The filtrate was extracted with ethyl acetate (2 x 30 ml). The organic extracts were combined, washed with brine and dried over Na2S04,filtered and evaporated under vacuum to give [77] as dark brown solid ( 1.3g), which upon further washing with ether yielded [77] as a brown solid ( 1.15 g, 76 %). ESIMS: 345 (M+ + l )

Reference： [1]Patent: WO2017/24021,2017,A1 .Location in patent: Paragraph 0703; 0704
[2]Patent: WO2017/24004,2017,A1 .Location in patent: Paragraph 0685
[3]Patent: WO2017/23980,2017,A1 .Location in patent: Paragraph 0685
[4]Patent: WO2017/23996,2017,A1 .Location in patent: Paragraph 0685
[5]Patent: WO2012/101654,2012,A2 .Location in patent: Page/Page column 59-60
[6]Patent: WO2014/16849,2014,A2 .Location in patent: Page/Page column 115; 116

9
[ 1228014-35-4 ]
1-(1-(3-methoxyphenyl)ethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2(3H)-one [ No CAS ]
racemic 1-(4-(1H-pyrrolo[2,3-b]pyridin-4-yl)phenyl)-3-(1-(3-methoxyphenyl)ethyl)-1H-imidazol-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 16h;Inert atmosphere;	The mixture of tert-butyl 4-bromo- 1 H-pyrrolo [2,3-bj pyridine- 1 -carboxylate (100 mg, 0.337 mmol) and 1 -(1 -(3 -methoxyphenyl)ethyl)-3 -(4-(4,4,5 ,5 -tetramethyl- 1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2(3H)-one (170 mg, 0.404 mmol) and K2C03 (140 mg, 1.010 mmol) in 1,4-dioxane (5 mL) and water (0.5 mL) was degassed by purging N2 gas. 1,1 ?-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (13.74 mg, 0.017 mmol) was added and the mixture was heated at 90 C for 16 h. The reaction mixture was filtered through CELITE, and thefiltrate was diluted with ethyl acetate. The organic phase was washed with water followed by brine and concentrated. The crude product was purified by preparative HPLC to afford the racemate compound as an off-white solid. This enantiomers were separated by SFC using column CHIRALPAK AS-H (250 x 21)mm, Sji Co-solvent in 20% methanol to afford Example 325 (Enantiomer 1, 17 mg, 0.04 1 mmol, 12.25% yield) as an off-whitesolid. MS(ESI) m/z:41 1.2; ?H NMR (400MHz, DM5 O-d6) oe ppm = 11.80 (br. s., 1H),8.29 (d, J=5.0 Hz, 1H), 8.00 - 7.91 (m, 2H), 7.89 - 7.81 (m, 2H), 7.60 - 7.51 (m, 1H),7.29 (t, J8.0 Hz, 1H), 7.21 (t, J4.3 Hz, 2H), 7.04 (d, J=3.0 Hz, 1H), 6.97 - 6.83 (m,3H), 6.64 (dd, J=3.5, 1.5 Hz, 1H), 5.36 (q, J=7.4 Hz, 1H), 3.76 (s, 3H), 1.70 (d, J=7.0 Hz,3H); HPLC: RT: 7.236 mm, 99.887% (Method G); RT: 8.408 mm, 99.526% (Method H);Chiral purity: 100% ee (RT 11.88 mm), determined by chiral SFC analysis column:CHIRALPAK OJ-H (250 x 4.6)mm, si?, Mobile Phase: 20% (0.2% DEA in methanol).; SOR: [cLj25?D= -164 (c 0.05, MeOH), and to afford Example 326 (Enantiomer 2, 10 mg, 0.024 mmol, 7.15% yield) as an off-white solid. MS(ESI) m/z:41 1.2; ?H NMR (400MHz,DMSO-d6) oe ppm 11.85 (s, 1H), 8.29 (d, J=5.0 Hz, 1H), 7.97 - 7.92 (m, 2H), 7.88 - 7.83(m, 2H), 7.56 (d, J=3.5 Hz, 1H), 7.30 (t, J=8.0 Hz, 1H), 7.23 - 7.19 (m, 2H), 7.04 (d,J=3.0 Hz, 1H), 6.95 - 6.90 (m, 2H), 6.87 (d, J=9.0 Hz, 1H), 6.64 (d, J=3.5 Hz, 1H), 5.41 -5.31 (m, 1H), 3.76 (s, 3H), 1.70 (d, J=7.5 Hz, 3H); HPLC: RT: 7.224 mm, 99.390%(Method G); RT: 7.893 mm, 98.767% (Method H); Chiral purity: 98.1366% ee(RT13.27mm), determined by chiral SFC analysis column: CHIRALPAK OJ-H (2504.6)mm, si?, Mobile Phase: 20% (0.2% DEA in methanol); SOR; [cLj253D= +152 (c 0.05, MeOH).

Reference： [1]Patent: WO2016/112236,2016,A1 .Location in patent: Page/Page column 376; 378; 379

10
[ 1228014-35-4 ]
(1-(tert-butoxycarbonyl)-4-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)boronic acid [ No CAS ]

Reference： [1]Patent: WO2017/24021,2017,A1
[2]Patent: WO2017/24004,2017,A1
[3]Patent: WO2017/23980,2017,A1
[4]Patent: WO2017/23996,2017,A1

11
[ 1228014-35-4 ]
tert-butyl 4-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/24021,2017,A1
[2]Patent: WO2017/24004,2017,A1
[3]Patent: WO2017/23980,2017,A1
[4]Patent: WO2017/23996,2017,A1

12
[ 1228014-35-4 ]
(1-(tert-butoxycarbonyl)-4-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)boronic acid [ No CAS ]

Reference： [1]Patent: WO2017/24021,2017,A1
[2]Patent: WO2017/24004,2017,A1
[3]Patent: WO2017/23980,2017,A1
[4]Patent: WO2017/23996,2017,A1

13
[ 1228014-35-4 ]
[ 768-35-4 ]
tert-butyl 4-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 60℃; for 5h;Inert atmosphere;	j0696j To a solution of tert-butyl 4-bromo-1H-pyrrolo[2,3-bjpyridine-1-carboxylate (XCII) (1.5 g, 5.1 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (XCIII) (1.07 g, 7.65 mmol, 1.1 eq) in a mixture solvent of dioxane (18 mL) and water (6 mL) was added K3P04 (2.11 g, 15.3mmol, 2.5 eq). The suspension was purged with nitrogen (x 3) followed by addition of Pd(dppf)C12 (373 mg, 0.51 mmol, 0.1 eq). The reaction was stirred at 60C for 5 h. The suspension was poured into water(10 mL) and extracted with EtOAc (10 mL x 3). The combined organic layer was washed with brine (5 mL), dried over Na2SO4 and concentrated under reduced pressure. Then the crude product was purified by column chromatography on silica gel to afford tert-butyl 4-(3- fluorophenyl)-1H-pyrrolo[2,3-bjpyridine-1-carboxylate (XCIV) as a white solid (1.37 g, 4.39 mmol, 86.0% yield). ?HNMR(CDC13, 400 MHz) ppm 1.69 (s, 9H), 6.68 (d, J=4Hz, 1H), 7.17 (dt, J=2Hz, J8.4Hz, 1H), 7.25 (d, J4.8Hz, 1H), 7.35 (d, J12Hz, 1H), 7.41 - 7.53 (m, 2H), 7.70 (d, J=4Hz, 1H), 8.57 (d, J4.8Hz, 1H); ESIMS found for C,8H,7FN202 mlz 313.1 (M+H).
86%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 60℃; for 5h;Inert atmosphere;	To a solution of fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (LXXV) (1.5 g, 5.1 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (LXXVI) (1.07 g, 7.65 mmol, 1.1 eq) in a mixture solvent of dioxane (18 mL) and water (6 mL) was added K3PO4 (2.11 g, 15.3 mmol, 2.5 eq). The suspension was purged with nitrogen (x 3) followed by addition of Pd(dppf)Cl2 (373 mg, 0.51 mmol, 0.1 eq). The reaction was stirred at 60C for 5 h. The suspension was poured into water (10 mL) and extracted with EtOAc (10 mL x 3). The combined organic layer was washed with brine (5 mL), dried over Na2S04 and concentrated under reduced pressure. Then the crude product was purified by column chromatography on silica gel to afford fert-butyl 4-(3-fluorophenyl)-lH-pyrrolo[2,3-b]pyridine- l-carboxylate (XLXXVII) as a white solid (1.37 g, 4.39 mmol, 86.0% yield). NMR (CDC13, 400 MHz) delta ppm 1.69 (s, 9H), 6.68 (d, J=4Hz, 1H), 7.17 (dt, J=2Hz, J=8.4Hz, 1H), 7.25 (d, J=4.8Hz, 1H), 7.35 (d, J=12Hz, 1H), 7.41 - 7.53 (m, 2H), 7.70 (d, J=4Hz, 1H), 8.57 (d, J=4.8Hz, 1H); ESIMS found for C18H17FN2O2 mlz 313.1 (M+H).
86%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 60℃; for 5h;Inert atmosphere;	Step 2 [0677] To a solution of fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (LXXV) (1.5 g, 5.1 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (LXXVI) (1.07 g, 7.65 mmol, 1.1 eq) in a mixture solvent of dioxane (18 mL) and water (6 mL) was added K3PO4 (2.11 g, 15.3 mmol, 2.5 eq). The suspension was purged with nitrogen (x 3) followed by addition of Pd(dppf)Cl2 (373 mg, 0.51 mmol, 0.1 eq). The reaction was stirred at 60C for 5 h. The suspension was poured into water (10 mL) and extracted with EtOAc (10 mL x 3). The combined organic layer was washed with brine (5 mL), dried over Na2SC>4 and concentrated under reduced pressure. Then the crude product was purified by column chromatography on silica gel to afford fert-butyl 4-(3-fluorophenyl)-lH-pyrrolo[2,3-b]pyridine-l-carboxylate (XLXXVII) as a white solid (1.37 g, 4.39 mmol, 86.0% yield). NMR (CDC13, 400 MHz) delta ppm 1.69 (s, 9H), 6.68 (d, J=4Hz, 1H), 7.17 (dt, J=2Hz, J=8.4Hz, 1H), 7.25 (d, J=4.8Hz, 1H), 7.35 (d, J=12Hz, 1H), 7.41 - 7.53 (m, 2H), 7.70 (d, J=4Hz, 1H), 8.57 (d, J=4.8Hz, 1H); ESIMS found for C18H17FN2O2 mlz 313.1 (M+H).

86%

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 60℃; for 5h;Inert atmosphere;

To a solution of fert-butyl 4-bromo-lH-pyrrolo[2,3-b]pyridine- l-carboxylate (LXXV) (1.5 g, 5.1 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (LXXVI) (1.07 g, 7.65 mmol, 1.1 eq) in a mixture solvent of dioxane (18 mL) and water (6 mL) was added K3PO4 (2.11 g, 15.3 mmol, 2.5 eq). The suspension was purged with nitrogen (x 3) followed by addition of Pd(dppf)Cl2 (373 mg, 0.51 mmol, 0.1 eq). The reaction was stirred at 60C for 5 h. The suspension was poured into water (10 mL) and extracted with EtOAc ( 10 mL x 3). The combined organic layer was washed with brine (5 mL), dried over Na2S04 and concentrated under reduced pressure. Then the crude product was purified by column chromatography on silica gel to afford fert-butyl 4-(3-fluorophenyl)-lH-pyrrolo[2,3-b]pyridine- l-carboxylate (XLXXVII) as a white solid (1.37 g, 4.39 mmol, 86.0% yield). NMR (CDC13, 400 MHz) delta ppm 1.69 (s, 9H), 6.68 (d, J=4Hz, 1H), 7.17 (dt, J=2Hz, J=8.4Hz, 1H), 7.25 (d, J=4.8Hz, 1H), 7.35 (d, J=12Hz, 1H), 7.41 - 7.53 (m, 2H), 7.70 (d, J=4Hz, 1H), 8.57 (d, J=4.8Hz, 1H); ESIMS found for C18H17FN2O2 mlz 313.1 (M+H).

Reference： [1]Patent: WO2017/24021,2017,A1 .Location in patent: Paragraph 0694; 0696
[2]Patent: WO2017/24004,2017,A1 .Location in patent: Paragraph 0677
[3]Patent: WO2017/23980,2017,A1 .Location in patent: Paragraph 0677
[4]Patent: WO2017/23996,2017,A1 .Location in patent: Paragraph 0677

14
[ 1228014-35-4 ]
[ 73183-34-3 ]
(1-(tert-butoxycarbonyl)-1H-pyrrolo[2.3-b]pyridin-4-yl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere;	To a stirred solution of <strong>[1228014-35-4]tert-butyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate</strong> (340 mg, 0.973 mmol, 85 % wtj, potassium acetate (432 mg, 4.40 mmol) and PdCI2(dppf) (215 mg, 0.294 mmol) in 1,4-dioxane (2.5 mL) was added 4,4,4T,4T,5,5,5T,5T-octamethyl-2, 2T-bi(1,3, 2-d ioxaborolane) (745 mg,2.93 mmol). The reaction mixture was purged with N2 and stirred at 100 C for 20 hours. The reaction mixture was partitioned between EtOAc (15 mL) and water (15 mL). The layers were separated andthe aqueous layer was extracted with further portions of EtOAc (15 x 2 mL). The combined organic phases were dried (hydrophobic frit) then concentrated in vacuoto give (1-(tert-butoxycarbonyl)-1H- pyrrolo[2,3-b]pyridin-4-yl)boronic acid (204 mg, 0.195 mmol, 20.01 % yield, ?25% purity) as a black oil.LCMS (2 mm Formic): Rt = 0.77 mi [MH] = 263.3

Reference： [1]Patent: WO2017/202742,2017,A1 .Location in patent: Page/Page column 82

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P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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. 1228014-35-4 ] {[proInfo.proName]}

Quality Control of [ 1228014-35-4 ]

Related Doc. of [ 1228014-35-4 ]

Product Details of [ 1228014-35-4 ]

Safety of [ 1228014-35-4 ]

Application In Synthesis of [ 1228014-35-4 ]

[ 1228014-35-4 ] Synthesis Path-Upstream 1~1

[ 1228014-35-4 ] Synthesis Path-Downstream 1~14

Related Functional Groups of [ 1228014-35-4 ]

Bromides

Amides

Related Parent Nucleus of [ 1228014-35-4 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1228014-35-4 ]

Related Parent Nucleus of
[ 1228014-35-4 ]