Home Cart Sign in  
Chemical Structure| 1010100-26-1 Chemical Structure| 1010100-26-1
Chemical Structure| 1010100-26-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

Lenalidomide-5-Br is a Lenalidomide-based E3 ubiquitin ligase cereblon ligand that can be conjugated to a protein ligand via a linker to form a PROTAC molecule.

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations

William F. Tracy ; Geraint H. M. Davies ; Lauren N. Grant ; Jacob M. Ganley ; Jesus Moreno ; Emily C. Cherney , et al.

Abstract: Immunomodulatory imide drugs form the core of many pharmaceutically relevant structures, but Csp2–Csp2 bond formation via metal-catalyzed cross coupling is difficult due to the sensitivity of the glutarimide ring ubiquitous in these structures. We report that replacement of the traditional alkali base with a fluoride source enhances a previously challenging Suzuki–Miyaura coupling on glutarimide-containing compounds with trifluoroborates. These enabling conditions are reactive enough to generate these derivatives in high yields but mild enough to preserve both the glutarimide and its sensitive stereocenter. Experimental and computational data suggest a mechanistically distinct process of π-coordination of the trifluoroborate enabled by these conditions.

Alternative Products

Product Details of Lenalidomide-5-Br

CAS No. :1010100-26-1
Formula : C13H11BrN2O3
M.W : 323.14
SMILES Code : O=C(C(N(CC1=C2C=CC(Br)=C1)C2=O)CC3)NC3=O
MDL No. :MFCD32263142
InChI Key :CMRQAKJTXKOGSF-UHFFFAOYSA-N
Pubchem ID :69049011

Safety of Lenalidomide-5-Br

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of Lenalidomide-5-Br

* 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 [ 1010100-26-1 ]

[ 1010100-26-1 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 454482-11-2 ]
  • [ 1010100-26-1 ]
  • 3-(5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 90℃; for 16h;Inert atmosphere; A stirred solution of 1c (50 mg, 0.22 mmol) in DMF (3.0 mL) in a sealed tube was purged with argon for 5 min prior to the addition of <strong>[454482-11-2]1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine</strong> (4a, 55 mg, 0.24 mmol), K3PO4 (94 mg, 0.44 mmol), and Pd(dppf)Cl2.DCM (9 mg, 0.011 mmol). The resulting mixture was then purged with argon for 5 min and then heated to 90° C. for 16 h. The reaction mixture was cooled to rt and then concentrated under reduced pressure. The crude material was purified by preparative TLC eluting with 10percent MeOH/DCM to afford I-163 as an off white solid (9.0 mg, 0.03 mmol, 12percent yield). MS [M+H]+=340.3. 1H NMR (DMSO-d6, 400 MHz): delta 7.68 (d, J=8.0 Hz, 1H), 7.63 (s, 1H), 7.58 (d, J=9.2 Hz, 1H), 6.28 (brs, 1H), 5.00 (dd, J=13.2 Hz, 5.2 Hz, 1H), 4.45 (d, J=17.6 Hz, 1H), 4.31 (d, J=17.6 Hz, 1H), 3.07 (brs, 2H), 2.68-2.60 (m, 4H), 2.35-2.32 (m, 2H), 2.27 (s, 3H) 2.06-1.99 (m, 1H)
  • 2
  • [ 1010100-26-1 ]
  • [ 121282-70-0 ]
  • tert-butyl ((1S,2S)-2-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)oxy)cyclohexyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With Quinuclidine; (1,2-dimethoxyethane)dichloronickel(II); [4,4?-bis(1,1-dimethylethyl)-2,2?-bipyridine-N1,N1?]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; potassium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine; In acetonitrile; at 20℃; for 70h;Inert atmosphere; Irradiation; Step 1. tert-butyl ((1S,2S)-2-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)oxy)cyclohexyl)carbamate (13-2a) To 3-(5-bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione (I-1d, 1600 mg, 4.95 mmol), <strong>[121282-70-0]tert-butyl ((1S,2S)-2-hydroxycyclohexyl)carbamate</strong> (13-1a, 1066 mg, 4.95 mmol), NiCl2(glyme) (54 mg, 0.25 mmol), dtbbpy (66 mg, 0.25 mmol), Ir[(dF(CF3)ppy)2dtbbpy]PF6 (56 mg, 0.050 mmol), quinuclidine (55 mg, 0.50 mmol) and K2CO3 (684 mg, 4.95 mmol) under an atmosphere of nitrogen was added MeCN (30 mL) and the resulting mixture was then stirred vigorously for 70 h under irradiation of blue LED light at room temperature. The reaction mixture was then diluted with DCM (20 mL), filtered, and concentrated to dryness. The crude material was purified by silica gel chromatography eluting with 0% to 3% MeOH in DCM to afford 13-2a (282 mg, 0.616 mmol, 12% yield) as a white powder. MS [M-tBu+H]+=402.3. 1H NMR (400 MHz, Chloroform-d) delta 7.97 (s, 1H), 7.82-7.70 (m, 1H), 7.13-6.92 (m, 2H), 5.19 (dd, J=13.2, 5.2 Hz, 1H), 4.56 (t, J=7.4 Hz, 1H), 4.42 (d, J=15.8 Hz, 1H), 4.27 (d, J=15.8 Hz, 1H), 4.23-4.16 (m, 1H), 3.78-3.66 (m, 1H), 2.95-2.74 (m, 2H), 2.33 (qd, J=13.0, 5.0 Hz, 1H), 2.25-2.16 (m, 2H), 2.14-2.04 (m, 2H), 1.85-1.74 (m, 1H), 1.46-1.33 (m, 3H), 1.41 (s, 9H).
  • 3
  • [ 1010100-26-1 ]
  • [ 121282-70-0 ]
  • tert-butyl ((1R,2S)-2-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)oxy)cyclohexyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With Quinuclidine; 2,2,6,6-tetramethyl-piperidine; (1,2-dimethoxyethane)dichloronickel(II); [4,4?-bis(1,1-dimethylethyl)-2,2?-bipyridine-N1,N1?]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; potassium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine; In acetonitrile; at 20℃; for 16h;Inert atmosphere; Irradiation; Step 1. tert-butyl ((1R,2S)-2-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)oxy)cyclohexyl)carbamate (38-2a) To a suspension of 1-Id (432 mg, 1.34 mmol)), tert-butyl ((1S,2S)-2-hydroxycyclohexyl) carbamate (38-1a, 1066 mg, 4.95 mmol), NiCl2(glyme) (54 mg, 0.25 mmol), dtbbpy (66 mg, 0.2548 mmol), Ir[(dF(CF3)ppy)2dtbbpy]PF6 (15 mg, 0.013 mmol) in MeCN (4.5 mL) under an atmosphere of nitrogen was added 2,2,6,6-tetramethylpiperidine (40-2, 226 muL, 1.34 mmol) and the resulting mixture was then stirred vigorously for 16 h under irradiation of blue LED light at room temperature. The reaction mixture was then diluted with EtOAc (20 mL), filtered, and concentrated to dryness. The crude material was purified by silica gel chromatography eluting with 0% to 100% EtOAc in heptanes to afford 38-2a (115 mg, 0.251 mmol, 19% yield) as a white powder. MS [M+H]+=458.3.
  • 4
  • [ 1010100-26-1 ]
  • [ 454170-16-2 ]
  • tert-butyl ((1R,2R)-2-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)oxy)cyclopentyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With 2,2,6,6-tetramethyl-piperidine; (1,2-dimethoxyethane)dichloronickel(II); [4,4?-bis(1,1-dimethylethyl)-2,2?-bipyridine-N1,N1?]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; In acetonitrile; at 20℃;Irradiation; Inert atmosphere; Step 1. tert-butyl ((1R,2R)-2-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)oxy)cyclopentyl)carbamate (24-2a) To a stirred suspension of 1-Id (263 mg, 0.813 mmol), <strong>[454170-16-2]tert-butyl ((1R,2R)-2-hydroxycyclopentyl)carbamate</strong> (24-1a, 149 mg, 0.740 mmol), NiCl2(glyme) (9 mg, 0.04 mmol), dtbbpy (11 mg, 0.042 mmol), and Ir[(dF(CF3)ppy)2dtbbpy]PF6 (10 mg, 9.1 mumol) in MeCN (2.5 mL) under an atmosphere of nitrogen was added 2,2,6,6-tetramethylpiperidine (40-2, 0.13 mL, 0.77 mmol) and the resulting mixture was stirred vigorously overnight under irradiation of blue LED light at room temperature. The reaction mixture was then diluted with EtOAc, filtered through Celite, and concentrated to dryness. The crude material was purified by reverse phase HPLC (eluting with MeCN/H2O with 0.1% formic acid). The fractions containing the desired product were combined and lyophilized to afford 24-2a as a white solid (30.8 mg, 0.067 mmol, 9% yield). MS [M+H]+=444.5. 1H NMR (400 MHz, DMSO-d6) delta 10.95 (s, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.18 (s, 1H), 7.11-6.99 (m, 2H), 5.07 (ddd, J=13.4, 5.2, 1.9 Hz, 1H), 4.72-4.56 (m, 1H), 4.52-4.16 (m, 2H), 3.88 (s, 1H), 2.90 (ddd, J=18.3, 13.6, 5.4 Hz, 1H), 2.60 (dd, J=3.8, 1.8 Hz, 1H), 2.38 (dd, J=13.2, 4.5 Hz, 1H), 2.14-1.83 (m, 3H), 1.83-1.58 (m, 3H), 1.50 (dq, J=13.5, 7.1, 6.5 Hz, 1H), 1.38 (s, 9H).
  • 5
  • [ 845305-83-1 ]
  • [ 1010100-26-1 ]
  • tert-butyl 4-((1-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)piperidin-4-yl)oxy)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
26 mg With palladium diacetate; caesium carbonate; XPhos; In 1,4-dioxane; at 100℃;Inert atmosphere; tert-butyl 4-((piperidin-4-yl)oxy)piperidine-1-carboxylate (200 mg, 0.7 mmol) was dissolved in dioxane (10 mL). 3-(5-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione (226 mg, 0.7 mmol), X-phos (100 mg, 0.21 mmol), cesium carbonate (456 mg, 1.4 mmol) and palladium acetate (31.4 mg, 0.14 mmol) were added. The mixture was heated to 100 C. and reacted overnight under nitrogen protection. The reaction solution was concentrated and then purified by column chromatography to yield a product of 26 mg. [M+H]+=527.3.
 

Historical Records

Technical Information

Categories