Structure of 943323-65-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 943323-65-7 |
Formula : | C7H6BrN3 |
M.W : | 212.05 |
SMILES Code : | NC1=CNC2=NC=CC(Br)=C21 |
MDL No. : | MFCD09880125 |
InChI Key : | RWOSDAABDCYOQZ-UHFFFAOYSA-N |
Pubchem ID : | 24729563 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.5% | With tin(II) chloride dihdyrate; hydrogen bromide In water at 70℃; for 1 h; | 4-Bromo-3-nitro-1H-pyrrolo[2,3-b]pyridine (500mg, 2.07mmol) was heated in 48percent aqueous hydrobromic acid (4mL) at 70°C and then tin (II) chloride dihydrate(2.26g, 10mmol) was added in portions. After addition the reaction was heated at 70°C for a further 1 hour and then cooled before carefully adding to stirring ice/H20 (l5mL). This solution was basified to pH 12 using sodium hydroxidesolution, and the insoluble material separated via filtration. The filtrate wasextracted with DCM (3xlOOmL) and the combined extracts were washed with H2O and saturated aqueous sodium chloride, dried (Mg504) and concentrated in vacuo. This afforded the desired compound, 230mg, 52.5percent, which was used without further purification. |
52.5% | With tin(II) chloride dihdyrate; hydrogen bromide In water at 70℃; for 1 h; | 4-Bromo-3-nitro-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.07 mmol) was heated in 48percent aqueous hydrobromic acid (4 mL) at 70° C. and then tin (II) chloride dihydrate (2.26 g, 10 mmol) was added in portions. After addition the reaction was heated at 70° C. for a further 1 hour and then cooled before carefully adding to stirring ice/H2O (15 mL). This solution was basified to pH12 using sodium hydroxide solution, and the insoluble material separated via filtration. The filtrate was extracted with DCM (3*100 mL) and the combined extracts were washed with H2O and saturated aqueous sodium chloride, dried (MgSO4) and concentrated in vacuo. This afforded the desired compound, 230 mg, 52.5percent, which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 25.0℃; for 12.0h; | To a solution of 4-bromo-1 H-pyrrolo[2,3-b]pyridin-3-amine (220 mg, 1.04 mmol)[prepared according to Example 89], 3-furoic acid (128 mg, 1.14 mmol) and diisopropylethyl amine (595 mul_, 3.42 mmol) in DCM (10 mL) at 25 C was added PyBrop (580 mg, 1.25 mmol) in one portion. After 12h, the solution was partitioned between H2O/DCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and purified using column chromatography (silica, 3% MeOH in DCM) affording the title compound (290 mg, 91%) as an orange oil: LC-MS (ES) m/z = 307 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 80.0℃; for 12.0h; | To a solution of 4-bromo-1 H-pyrrolo[2,3-b]pyridin-3-amine (63 mg, 0.298 mmol) in dioxane (2.5 mL) and H2O (0.5 ml_) was added 1 ,1-dimethylethyl [3- phenyi-2-([5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2- thienyl]carbonyl}amino)propyl]carbamate (145 mg, 0.298 mmol)[prepared inExample 87], Pd(PPh3)4 (17 mg, 14.9 mumol) and K2CO3 (164 mg, 1.19 mmol). After heating to 800C for 12h in a sealed tube, the reaction solution was partitioned between H2CVDCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and purified using column chromatography (silica, 3% MeOH in DCM) affording the title compound (60 mg, 41 %) as an orange oil: LC-MS (ES) m/z = 492 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.5% | With tin(II) chloride dihdyrate; hydrogen bromide; In water; at 70.0℃; for 1.0h; | 4-Bromo-3-nitro-1H-pyrrolo[2,3-b]pyridine (500mg, 2.07mmol) was heated in 48% aqueous hydrobromic acid (4mL) at 70C and then tin (II) chloride dihydrate(2.26g, 10mmol) was added in portions. After addition the reaction was heated at 70C for a further 1 hour and then cooled before carefully adding to stirring ice/H20 (l5mL). This solution was basified to pH 12 using sodium hydroxidesolution, and the insoluble material separated via filtration. The filtrate wasextracted with DCM (3xlOOmL) and the combined extracts were washed with H2O and saturated aqueous sodium chloride, dried (Mg504) and concentrated in vacuo. This afforded the desired compound, 230mg, 52.5%, which was used without further purification. |
52.5% | With tin(II) chloride dihdyrate; hydrogen bromide; In water; at 70.0℃; for 1.0h; | 4-Bromo-3-nitro-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.07 mmol) was heated in 48% aqueous hydrobromic acid (4 mL) at 70 C. and then tin (II) chloride dihydrate (2.26 g, 10 mmol) was added in portions. After addition the reaction was heated at 70 C. for a further 1 hour and then cooled before carefully adding to stirring ice/H2O (15 mL). This solution was basified to pH12 using sodium hydroxide solution, and the insoluble material separated via filtration. The filtrate was extracted with DCM (3*100 mL) and the combined extracts were washed with H2O and saturated aqueous sodium chloride, dried (MgSO4) and concentrated in vacuo. This afforded the desired compound, 230 mg, 52.5%, which was used without further purification. |
With hydrogen bromide; tin(ll) chloride; In water; at 70.0℃; for 1.0h;pH ~ 12; | SnCI2 (4.4 g, 23.0 mmol) was added portion-wise to a 70 0C solution of 4- bromo-3-nitro-1 H-pyrrolo[2,3-b]pyridine (1 g, 4.12 mmol) in cone. HBr (7 mL). After 1 h, the solution was added over ice and the pH adjusted to -12. The precipitate was filtered and the aqueous residue was washed with excess DCM. The <n="156"/>combined organic fractions were dried over Na2SO4, concentrated and used directly. LC-MS (ES) m/z 213 (M+H)+. |
Tags: 943323-65-7 synthesis path| 943323-65-7 SDS| 943323-65-7 COA| 943323-65-7 purity| 943323-65-7 application| 943323-65-7 NMR| 943323-65-7 COA| 943323-65-7 structure
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