Home Cart Sign in  
Chemical Structure| 226085-18-3 Chemical Structure| 226085-18-3

Structure of 226085-18-3

Chemical Structure| 226085-18-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

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

Alternative Products

Product Details of [ 226085-18-3 ]

CAS No. :226085-18-3
Formula : C14H11BrN2O2S
M.W : 351.22
SMILES Code : CC1=CC=C(C=C1)S(=O)(=O)N1C=C(Br)C2=CC=CN=C12
MDL No. :MFCD10697518
InChI Key :NDJOLIOBEZICFO-UHFFFAOYSA-N
Pubchem ID :21669155

Safety of [ 226085-18-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 226085-18-3 ]

* 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 [ 226085-18-3 ]

[ 226085-18-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 5419-55-6 ]
  • [ 226085-18-3 ]
  • [ 882562-39-2 ]
YieldReaction ConditionsOperation in experiment
69.4% With n-butyllithium In tetrahydrofuran at -90 - -80℃; for 0.5 h; Large scale [0387] Example lc: l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-ylboronic acid (8a) [0388] THF (28.5 kg) and 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine (7a) (4 kg) were added to a 72 L flask. The mixture was stirred until the solid dissolved completely. Triisopropyl borate (3.2 kg) was added and the mixture was cooled to below -80 °C. n-BuLi (4.65 kg) was added drop wise at a rate of about 0.6-0.9 kg/hour maintaining the temperature of about -80 to -90 °C. After the addition, the temperature was maintained at -80 to -90 °C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the peak area of 3-bromo-l- tosyl-lH-pyrrolo[2,3-b]pyridine (7a) was less than 4percent. [0389] Water (2 kg) was slowly added to the mixture to quench the reaction. The mixture temperature returned to about 15-25 °C. The mixture was transferred to a 50 L reactor to be concentrated below 40 °C under vacuum of a pressure less than -0.08 MPa until no THF distilled out. The residue was dissolved into water (25 kg) and 10percent aqueous NaOH solution (26 kg). The mixture was stirred until the solid dissolved completely. The mixture was transferred into a vacuum filter and filtered. The filtrate was extracted twice with MTBE (21 kg each) at about 20-30 °C. During each extraction, the mixture was stirred 15 minutes and held 15 minutes. HC1 (28L) was added into the aqueous phase to adjust the pH to between 3 and 4 while maintaining the temperature of about 10-20 °C. The mixture was stirred at about 10-15 °C for 1 hour. The mixture was transferred into a centrifuge and filtered. The resultant cake after filtering was washed with water (5 kg) and petroleum ether (5 kg). The cake was dried at 35-45 °C until the LOD (loss on drying) was less than 3percent. An off-white solid resulted (2.5 kg and 98.8percent purity as measured by HPLC analysis (method A), 69.4percent yield of l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-ylboronic acid (8a)).
69.4% With n-butyllithium In tetrahydrofuran at -90 - -80℃; Large scale [00390] 1 -tosyl-1 H-pyrrolo[2,3-b]pyridin-3-ylboronic acid: [00391] THF (28.5 kg) and 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine (4 kg) were added to a 72L flask. The mixture was stirred until the solid dissolved completely. Triisopropyl borate (3.2 kg) was added and the mixture was cooled to below -80 °C. n-BuLi (4.65 kg) was added drop wise at a rate of about 0.6-0.9 kg/hour maintaining the temperature of about -80 to -90 °C. After the addition, the temperature was maintained at about -80 to -90 °C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the peak area of 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine was less than 4percent. Typical retention time for 1 -tosyl-1 H-pyrrolo[2,3-b]pyridin-3-ylboronic acid was 4.6 minutes. Extra triisopropyl borate and n-BuLi was added to lower the peak area of 3 -bromo-1 -tosyl-1 H-pyrrolo [2,3 -b]pyridine. [00392] Water (2 kg) was slowly added to the mixture to quench the reaction. The mixture temperature returned to about 15-25 °C. The mixture was transferred to a 50L reactor to be concentrated below 40 °C under vacuum of a pressure less than -0.08 MPa until no THF distilled out. The residue was dissolved into water (25 kg) and 10percent aqueous NaOH solution (26 kg). The mixture was stirred until the solid dissolved completely. The mixture was transferred into a vacuum filter and filtered. The filtrate was extracted twice with MTBE (21 kg each) at about 20-30 °C. During each extraction, the mixture was stirred 15 minutes and held 15 minutes. HC1 acid (28L) was added into the aqueous phase to adjust the pH to between 3 and 4 while maintaining the temperature of about 10-20 °C. The mixture was stirred at about 10-15 °C for 1 hour. The mixture was transferred into a centrifuge and filtered. The resultant cake after filtering was washed with water (5 kg) and petroleum ether (5 kg). The cake was dried at 35-45 °C until the LOD (loss on drying) was less than 3percent. An off-white solid resulted (2.5 kg and 98.8percent purity as measured by HPLC analysis (method A), 69.4percent yield of l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-ylboronic acid).
69.4%
Stage #1: With n-butyllithium In tetrahydrofuran at -90 - -80℃; Large scale
Stage #2: With water; sodium hydroxide In tetrahydrofuranLarge scale
[0275] l-tosyl-lH-pyrrolo[2, 3-b ]pyridin-3-ylboronic acid: [0276] THF (28.5 kg) and 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine (4 kg) were added to a 72L flask. The mixture was stirred until the solid dissolved completely. Triisopropyl borate (3.2 kg) was added and the mixture was cooled to below -80 °C. n-BuLi (4.65 kg) was added drop wise at a rate of about 0.6-0.9 kg/hour maintaining the temperature of about -80 to -90 °C. After the addition, the temperature was maintained at about -80 to -90 °C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the peak area of 3-bromo-l-tosyl- lH-pyrrolo[2,3-b]pyridine was less than 4percent. Typical retention time for 1-tosyl-lH- pyrrolo[2,3-b]pyridin-3-ylboronic acid was 4.6 minutes. Extra triisopropyl borate and n-BuLi was added to lower the peak area of 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine. [0277] Water (2 kg) was slowly added to the mixture to quench the reaction. The mixture temperature returned to about 15-25 °C. The mixture was transferred to a 50L reactor to be concentrated below 40 °C under vacuum of a pressure less than -0.08 MPa until no THF distilled out. The residue was dissolved into water (25 kg) and 10percent aqueous NaOH solution (26 kg). The mixture was stirred until the solid dissolved completely. The mixture was transferred into a vacuum filter and filtered. The filtrate was extracted twice with MTBE (21 kg each) at about 20-30 °C. During each extraction, the mixture was stirred 15 minutes and held 15 minutes. HC1 acid (28L) was added into the aqueous phase to adjust the pH to between 3 and 4 while maintaining the temperature of about 10-20 °C. The mixture was stirred at about 10-15 °C for 1 hour. The mixture was transferred into a centrifuge and filtered. The resultant cake after filtering was washed with water (5 kg) and petroleum ether (5 kg). The cake was dried at 35-45 °C until the LOD (loss on drying) was less than 3percent. An off-white solid resulted (2.5 kg and 98.8percent purity as measured by HPLC analysis (method A), 69.4percent yield of l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-ylboronic acid).
References: [1] Patent: WO2013/6634, 2013, A2, . Location in patent: Paragraph 0387-0389.
[2] Patent: WO2013/70606, 2013, A1, . Location in patent: Paragraph 00390-00392.
[3] Patent: WO2014/74471, 2014, A1, . Location in patent: Paragraph 0275-0277.
  • 2
  • [ 226085-18-3 ]
  • [ 882562-39-2 ]
YieldReaction ConditionsOperation in experiment
69.4% With n-butyllithium; Triisopropyl borate In tetrahydrofuran at -90 - -80℃; Large scale [0397] 1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-ylboronic acid: [0398] THF (28.5 kg) and 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine (4 kg) were added to a 72L flask. The mixture was stirred until the solid dissolved completely. Triisopropyl borate (3.2 kg) was added and the mixture was cooled to below -80 °C. n-BuLi (4.65 kg) was added drop wise at a rate of about 0.6-0.9 kg/hour maintaining the temperature of about -80 to -90 °C. After the addition, the temperature was maintained at about -80 to -90 °C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the peak area of 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine was less than 4percent. Typical retention time for l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-ylboronic acid was 4.6 minutes. Extra triisopropyl borate and n-BuLi was added to lower the peak area of 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine. [0399] Water (2 kg) was slowly added to the mixture to quench the reaction. The mixture temperature returned to about 15-25 °C. The mixture was transferred to a 50 L reactor to be concentrated below 40 °C under vacuum of a pressure less than -0.08 MPa until no THF distilled out. The residue was dissolved into water (25 kg) and 10percent aqueous NaOH solution (26 kg). The mixture was stirred until the solid dissolved completely. The mixture was transferred into a vacuum filter and filtered. The filtrate was extracted twice with MTBE (21 kg each) at about 20-30 °C. During each extraction, the mixture was stirred 15 minutes and held 15 minutes. HC1 acid (28L) was added into the aqueous phase to adjust the pH to between 3 and 4 while maintaining the temperature of about 10-20 °C. The mixture was stirred at about 10-15 °C for 1 hour. The mixture was transferred into a centrifuge and filtered. The resultant cake after filtering was washed with water (5 kg) and petroleum ether (5 kg). The cake was dried at 35-45 °C until the LOD (loss on drying) was less than 3percent. An off-white solid resulted (2.5 kg and 98.8percent purity as measured by HPLC analysis (method A), 69.4percent yield of l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-ylboronic acid).
References: [1] Patent: WO2014/201332, 2014, A1, . Location in patent: Paragraph 0397-0399.
  • 3
  • [ 7732-18-5 ]
  • [ 73183-34-3 ]
  • [ 226085-18-3 ]
  • [ 866545-91-7 ]
  • [ 882562-39-2 ]
References: [1] Patent: US2018/179199, 2018, A1, . Location in patent: Paragraph 0449-0450.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 226085-18-3 ]

Aryls

Chemical Structure| 479552-71-1

A448475 [479552-71-1]

5-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.98

Chemical Structure| 1036028-16-6

A512412 [1036028-16-6]

3-Bromo-5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.96

Chemical Structure| 348640-07-3

A155769 [348640-07-3]

4-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.95

Chemical Structure| 880769-95-9

A302094 [880769-95-9]

3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.95

Chemical Structure| 1001070-33-2

A740408 [1001070-33-2]

5-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.93

Bromides

Chemical Structure| 479552-71-1

A448475 [479552-71-1]

5-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.98

Chemical Structure| 1036028-16-6

A512412 [1036028-16-6]

3-Bromo-5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.96

Chemical Structure| 348640-07-3

A155769 [348640-07-3]

4-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.95

Chemical Structure| 880769-95-9

A302094 [880769-95-9]

3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.95

Chemical Structure| 1001070-33-2

A740408 [1001070-33-2]

5-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.93

Sulfamides

Chemical Structure| 479552-71-1

A448475 [479552-71-1]

5-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.98

Chemical Structure| 1036028-16-6

A512412 [1036028-16-6]

3-Bromo-5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.96

Chemical Structure| 348640-07-3

A155769 [348640-07-3]

4-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.95

Chemical Structure| 880769-95-9

A302094 [880769-95-9]

3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.95

Chemical Structure| 1001070-33-2

A740408 [1001070-33-2]

5-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.93

Related Parent Nucleus of
[ 226085-18-3 ]

Other Aromatic Heterocycles

Chemical Structure| 479552-71-1

A448475 [479552-71-1]

5-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.98

Chemical Structure| 1036028-16-6

A512412 [1036028-16-6]

3-Bromo-5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.96

Chemical Structure| 348640-07-3

A155769 [348640-07-3]

4-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.95

Chemical Structure| 880769-95-9

A302094 [880769-95-9]

3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.95

Chemical Structure| 1001070-33-2

A740408 [1001070-33-2]

5-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Similarity: 0.93