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Chemical Structure| 207799-10-8
Chemical Structure| 207799-10-8
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Product Details of [ 207799-10-8 ]

CAS No. :207799-10-8 MDL No. :MFCD09037866
Formula : C10H13BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IRRRVCLDPODLJG-UHFFFAOYSA-N
M.W : 273.13 Pubchem ID :11680626
Synonyms :

Calculated chemistry of [ 207799-10-8 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.18
TPSA : 51.22 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 1.94
Log Po/w (SILICOS-IT) : 1.82
Consensus Log Po/w : 2.33

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.216 mg/ml ; 0.00079 mol/l
Class : Soluble
Log S (Ali) : -3.16
Solubility : 0.189 mg/ml ; 0.000694 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.83
Solubility : 0.0406 mg/ml ; 0.000149 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.52

Safety of [ 207799-10-8 ]

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

Application In Synthesis of [ 207799-10-8 ]

* 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 [ 207799-10-8 ]
  • Downstream synthetic route of [ 207799-10-8 ]

[ 207799-10-8 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 207799-10-8 ]
  • [ 84249-14-9 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: for 16 h;
2-Amino-4-bromopyridine (166)tert-Bxx\\y\\ carbamate 155 (200 mg, 0.73 mol) is suspended in water (1 mL) and treated with HBr (1 mL, 48 wt. percent in water). After stirring 16 h, the reaction mixture is poured onto aqueous NaHCO3 (25 mL) and extracted into EtOAc (3 x 25 mL). The combined EtOAc phases are dried (MgSO4) and reduced in vacuo. The title compound is obtained after chromatography of this residue (neat EtOAc).Yield: 73 mg (58percent).LC/MS tx 0.69 min.MS(ES+) m/z 175, 173 (M+H).
58%
Stage #1: With hydrogen bromide In water for 16 h;
Stage #2: With sodium hydrogencarbonate In water
Synthesis of Compound 3582-Amino-4-bromopyridine (166) <n="214"/>tert-Butyl carbamate 155 (200 mg, 0.73 mol) was suspended in water (1 mL) and treated with HBr (1 mL, 48 wt. percent in water). After stirring 16 h, the reaction mixture was poured onto aqueous NaHCO3 (25 mL) and extracted into EtOAc (3 x 25 mL). The combined EtOAc phases were dried (MgSO4) and reduced in vacuo. The title compound was obtained after chromatography of this residue (neat EtOAc). Yield: 73 mg (58percent). LC/MS tτ 0.69 min. MS(ES+) m/z 175, 173 (M+H).
58%
Stage #1: for 16 h;
2-Amino-4-bromopyridine (166); tert-Butyl carbamate 155 (200 mg, 0.73 mol) is suspended in water (1 mL) and treated with HBr (1 mL, 48 wt. percent in water). After stirring 16 h, the reaction mixture is poured onto aqueous NaHCO3 (25 mL) and extracted into EtOAc (3 x 25 mL). The combined EtOAc phases are dried (MgSO4) and reduced in vacuo. The title compound is obtained after chromatography of this residue (neat EtOAc). Yield: 73 mg (58percent). LC/MS tx 0.69 min. MS(ES+) m/z 175, 173 (M+H).
58%
Stage #1: for 16 h;
Stage #2: With sodium hydrogencarbonate In water
Synthesis of Compound 358; 2-Amino-4-bromopyridine (166); tert-Buty\\ carbamate 155 (200 mg, 0.73 mol) is suspended in water (1 mL) and treated with HBr (1 mL, 48 wt. percent in water). After stirring 16 h, the reaction mixture is poured onto aqueous NaHCO3 (25 mL) and extracted into EtOAc (3 x 25 mL). The combined EtOAc phases are dried (MgSO4) and reduced in vacuo. The title compound is obtained after chromatography of this residue (neat EtOAc). Yield: 73 mg (58percent). LC/MS tx 0.69 min. MS(ES+) m/z 175, 173 (M+H).

Reference: [1] Patent: WO2008/57497, 2008, A2, . Location in patent: Page/Page column 301
[2] Patent: WO2007/89669, 2007, A2, . Location in patent: Page/Page column 212-213
[3] Patent: WO2008/57469, 2008, A1, . Location in patent: Page/Page column 301
[4] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 301
[5] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 2
  • [ 84249-14-9 ]
  • [ 24424-99-5 ]
  • [ 207799-10-8 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -5℃; for 0.166667 h;
Stage #2: at 20℃; for 1 h;
A solution of 4-bromopyridin-2-amine (519 mg) in dry THF (15 mL) was treated with bis(trimethylsilyl)-amide (1 M in hexane, 6 mL) at −5° C. and the solution was stirred at this temperature for 10 minutes. Di-tert-butyl dicarbonate (654 mg) was added and the mixture was stirred at rt for 1 h. Saturated ammonium chloride solution (20 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were washed with water and brine, dried and the volatiles were removed under reduced pressure to yield the desired compound (96percent yield).
96%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -5℃; for 0.166667 h;
Stage #2: at 20℃; for 1 h;
Intermediate 20b) A solution of 4-bromopyridin-2-amine (519 mg) in dry THF (15 mL) was treated with bis(trimethylsilyl)- amide (1 M in hexane, 6 mL) at -5 °C and the solution was stirred at this temperature for 10 minutes. Di- ferf-butyl dicarbonate (654 mg) was added and the mixture was stirred at rt for 1 h. Saturated ammonium chloride solution (20 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were washed with water and brine, dried and the volatiles were removed under reduced pressure to yield the desired compound (96percent yield).
89% at 50℃; for 16 h; fe/f-butyl (4-bromopyridin-2-yl)carbamate (i5): To a stirred solution of 4-bromopyridin-2-amine (1 g, 5.7 mmol) in n-butanol (15 ml_), boc- anhydride (1 .7 ml_, 6.9 mmol) was added and the reaction was heated at 50°C for 16h. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was removed under reduced pressure to obtain a residue. The residue was dissolved in ethyl acetate and washed with water. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford fe/f-butyl (4-bromopyridin-2-yl)carbamate (i5) (1 .4 g, Yield 89percent). MS (ESI) m/e (M+1 )+: 273
57% With dmap In <i>tert</i>-butyl alcohol at 20℃; A 250 mL round bottom flask was added 4-bromo-2-amine (4-bromopyridin-2-amine) (5g, 28.90mmol), tert-butyl dicarbonate ((Boc)2O) (6.8g, 31.16mmol), 4-dimethylaminopyridine (4-dimethylaminopyridine) (0.32g), tert-butanol (tert-Butanol) (70mL). Was stirred overnight at room temperature, concentrated in vacuo, and the resulting mixture by volume of 5: 1 hexane / diethyl ether (hexane / ether) 30ml and washed to yield N- tert-butoxycarbonyl-4-bromo - pyridin-2-amine (tert-butylN - (4-bromopyridin-2-yl) carbamate) (4.5g, 57percent), as a white solid
1.2 g With dmap; triethylamine In tetrahydrofuran at 20℃; for 3 h; To a mixture of 4-bromo-pyridin-2-ylamine (2 g, 11.6 mmol), TEA (3.51 g, 34.8 mmol) and DMAP (100 mg) in THF (25 mL) was added Boc20 (3 g, 13.9 mmol) at room temperature. The solution was stirred at room temperature for 3 h, and then concentrated. The residue was purified by column chromatography to give (4-bromo-pyridin-2-yl)-carbamic acid tert-butyl ester (1.2 g) as a white solid.
6.4 g at 10 - 50℃; for 3 h; D)
t
To a suspension of 4-bromopyridin-2-amine (45 g) in tert-butanol (336 mL) was added di-tert-butyl dicarbonate (84 mL) at room temperature, the mixture was stirred at 50° C. for 3 hr, and the precipitate was collected by filtration.
The mother liquid was concentrated under reduced pressure, the residue was suspended in hexane, and the solid was collected by filtration.
The collected solids were combined, washed with diisopropyl ether, and dried under reduced pressure to give the title compound (56 g).
The filtrates were combined, and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.4 g).
MS (ESI+).
found: 217.0.

Reference: [1] Patent: US2014/194443, 2014, A1, . Location in patent: Paragraph 0541-0542
[2] Patent: WO2014/108337, 2014, A1, . Location in patent: Page/Page column 69
[3] Patent: WO2016/124508, 2016, A1, . Location in patent: Page/Page column 39
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5613 - 5637
[5] Patent: CN104744433, 2016, B, . Location in patent: Paragraph 0027; 0028
[6] Patent: WO2014/418, 2014, A1, . Location in patent: Page/Page column 30; 31
[7] Patent: WO2014/154723, 2014, A1, . Location in patent: Page/Page column 29
[8] Patent: US2015/133451, 2015, A1, . Location in patent: Paragraph 0910; 0911
[9] Patent: US2015/197511, 2015, A1, . Location in patent: Paragraph 0171; 0172
  • 3
  • [ 75-65-0 ]
  • [ 207799-10-8 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With diphenyl phosphoryl azide; triethylamine In toluene at 20℃; for 0.5 h;
Stage #2: at 90℃; for 2 h;
TEA (311 uL; 2.23 mmol) was added to a mixture of 4-bromo-picolinic acid (450 mg; 2.23 mmol) in toluene (6.7 mL). Diphenylphosphoryl azide (480 uL; 2.23 mmol) was added and the reaction was stirred for 30 min at RT, after which tert-butanol (427 uL; 4.46 mmol) was added. The reaction mixture was heated at 90° C. for 2 h, then was cooled to RT. The solution was diluted with EtOAc (15 mL), washed with 10percent aqueous Na2CO3 (3.x.3 mL) and brine (10 mL), dried (MgSO4) and concentrated in vacuo. The crude product was chromatographed (SiO2; continuous gradient from 0 to 75percent solvent B over 15 min, where solvent A=hexanes and solvent B=EtOAc) to give Part A compound (0.39 g; 65percent).
Reference: [1] Patent: US2008/9465, 2008, A1, . Location in patent: Page/Page column 44
  • 4
  • [ 30766-03-1 ]
  • [ 207799-10-8 ]
Reference: [1] Patent: WO2008/57497, 2008, A2, . Location in patent: Page/Page column 293
[2] Patent: WO2008/57469, 2008, A1, . Location in patent: Page/Page column 293
[3] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 293
  • 5
  • [ 30766-03-1 ]
  • [ 75-65-0 ]
  • [ 207799-10-8 ]
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 6
  • [ 18437-58-6 ]
  • [ 207799-10-8 ]
Reference: [1] Patent: WO2008/57469, 2008, A1,
[2] Patent: WO2008/57468, 2008, A1,
  • 7
  • [ 22282-99-1 ]
  • [ 207799-10-8 ]
Reference: [1] Patent: WO2008/57469, 2008, A1,
[2] Patent: WO2008/57468, 2008, A1,
  • 8
  • [ 5470-66-6 ]
  • [ 207799-10-8 ]
Reference: [1] Patent: WO2008/57469, 2008, A1,
[2] Patent: WO2008/57468, 2008, A1,
  • 9
  • [ 207799-10-8 ]
  • [ 73183-34-3 ]
  • [ 1095708-32-9 ]
YieldReaction ConditionsOperation in experiment
76% With potassium acetate In dimethyl sulfoxide at 85℃; for 1.25 h; Inert atmosphere Preparation 24terf-Butyl (4-bromopyhdin-2-yl)carbannate (0.494 g, 1 .81 mmol), bis(pinacolato)diboron (1 .4 g 5.51 mmol ) and potassium acetate (0.535 g , 5.45 mmol) were stirred in dimethylsulfoxide (8 ml_). The mixture was flushed with nitrogen for 10 minutes. [1 ,1 '- Bis(diphenylphosphino)ferrocene] dichloropalladium(ll) (0.150 g, 0.184 mmol) was added and the system flushed for a further 5 minutes with nitrogen before heating the reaction mixture to 85°C under nitrogen for 1 hour. The reaction mixture was diluted in ethyl acetate (15 ml_) and washed with aqueous hydrochloride solution (10 ml_, 0.2 M). Some of the product went into the aqueous layer and some stayed in the organic layer. The aqueous layer was treated with saturated aqueous sodium carbonate carefully until ~pH 6 was achieved then extracted with ethyl acetate (10 ml_). The organics were dried over sodium sulfate, filtered and concentrated in vacuo to give title compound as a white solid (0.44 g, 76percent).1HNMR (de -DMSO): δ 1 .29 (s, 12H), 1 .45 (s, 9H), 7.15-7.17 (d, 1 H), 8.07 (s, 1 H), 8.24- 8.25 (d, 1 H), 9.77 (s, 1 H)LCMS Rt = 0.68 min MS m/z 183.1 [MH]+
56% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 80℃; for 5 h; A solution of intermediate 20b (352 mg), potassium acetate (380 mg), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (360 mg) and Pd(dppf)Cl2.CH2Cl2 (105 mg) in dry DMF (10 mL) was stirred at 80° C. for 5 h. The volatiles were removed under reduced pressure, the residue dissolved in EtOAc and the organic layer was washed with water, dried and the volatiles were removed under reduced pressure. The crude product was purified through washing with heptane to yield the desired compound (56percent yield). LC-MS (Method 1): m/z [M (boronic acid)+H]+=239.2 (MW (boronic acid) calc.=238.05); Rt=2.3 min.
56% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 80℃; for 5 h; Intermediate 20c) A solution of intermediate 20b (352 mg), potassium acetate (380 mg), 4,4,4',4', 5,5,5', 5'-octamethyl-2,2'- bi(1 ,3,2-dioxaborolane) (360 mg) and Pd(dppf)CI2-CH2CI2 (105 mg) in dry DMF (10 mL) was stirred at 80 °C for 5 h. The volatiles were removed under reduced pressure, the residue dissolved in EtOAc and the organic layer was washed with water, dried and the volatiles were removed under reduced pressure. The crude product was purified through washing with heptane to yield the desired compound (56percent yield) LC- S (Method 1): m/z [M (boronic acid)+H]+ = 239.2 (MW (boronic acid) calc. = 238.05); R, = 2.3 min.
53% With potassium acetate In N,N-dimethyl-formamide at 80℃; for 2 h; Inert atmosphere Step 6.1.
tert-Butyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrid-2-yl]carbamate
To a solution of 6.76 (24.8 mmol) of tert-butyl (4-bromopyrid-2-yl)carbamate (Deady, Leslie W.; Korytsky, Olga L.; Rowe, Jeffrey E.; Aust. J. Chem.; 35; 10; 1982; 2025-2034) in 150 mL of dimethylformamide are added 8.0 g (81 mmol) of potassium acetate predried at 130° C. and 6.9 g (27 mmol) of bis(pinacolato)diboron.
A stream of argon is then sparged through for a few moments, and 1.2 g (1.5 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) are added.
The mixture is stirred at 80° C. under argon for 2 hours and then poured into saturated aqueous ammonium chloride solution.
The product is extracted with ethyl acetate, the organic phase is dried over sodium sulfate and the solvent is stripped off under reduced pressure.
The residue is triturated in 300 mL of refluxing diisopropyl ether and the insoluble matter is separated out by filtration.
The filtrate is cooled and partially concentrated under reduced pressure.
After adding 70 mL of hexane, the precipitate formed is isolated by filtration to give 4.2 g of an orange-colored solid after drying.
Yield: 53percent
m.p.: 188-193° C.
1H NMR (CDCl3) δ: 8.15 (m, 2H), 7.65 (broad s, 1H), 7.15 (d, 1H), 1.40 (s, 9H), 1.20 (s, 12H) ppm.

Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5613 - 5637
[2] Patent: WO2012/4714, 2012, A2, . Location in patent: Page/Page column 62
[3] Patent: US2014/194443, 2014, A1, . Location in patent: Paragraph 0543-0545
[4] Patent: WO2014/108337, 2014, A1, . Location in patent: Page/Page column 69; 70
[5] Patent: US2010/179154, 2010, A1, . Location in patent: Page/Page column 29
[6] Patent: WO2005/89763, 2005, A1, . Location in patent: Page/Page column 69-70
[7] Patent: US2011/312934, 2011, A1, . Location in patent: Page/Page column 13
[8] Patent: WO2016/124508, 2016, A1, . Location in patent: Page/Page column 39
  • 10
  • [ 207799-10-8 ]
  • [ 74-88-4 ]
  • [ 946000-13-1 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 16 h;
tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160)To a solution of te/7-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0°C is added sodium hydride (53 mg, 1.32 mmol, 60percent dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5percent citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The EPO <DP n="298"/>combined organic phases are dried over Na2SO4 and purified by column chromatography (70percent EtOAc in heptane) to give the title compound. Yield: 240 mg (76percent). LC/MS tr 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).
76%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 16 h;
Synthesis of Compound 357tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160)To a solution of tert-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0°C was added sodium hydride (53 mg, 1.32 mmol, 60percent dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane was added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction was then quenched with 5percent citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The combined organic phases were dried over Na2SO4 and purified by column chromatography (70percent EtOAc in heptane) to give the title compound. Yield: 240 mg (76percent). LC/MS ?r 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).
76%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 20℃; for 16 h;
tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160); To a solution of ter/-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0°C is added sodium hydride (53 mg, 1.32 mmol, 60percent dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5percent citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The EPO <DP n="298"/>combined organic phases are dried over Na2SO4 and purified by column chromatography (70percent EtOAc in heptane) to give the title compound. Yield: 240 mg (76percent). LC/MS tr 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).
76%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 16 h;
Synthesis of Compound 357; tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160); To a solution of tert-buty\\ carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0°C is added sodium hydride (53 mg, 1.32 mmol, 60percent dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5percent citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The EPO <DP n="298"/>combined organic phases are dried over Na2SO4 and purified by column chromatography (70percent EtOAc in heptane) to give the title compound. Yield: 240 mg (76percent). LC/MS ?r 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).
0.25 g
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 1 h;
Step a. To a solution of teit-butyl (4-bromopyridin-2-yl)carbamate (0.25g, 0.915 mmol) in DMF (5 ml) was added NaH (60percent in oil) (0.073g, 1.83 mmol) at 0°C. The reaction mixture was stirred at 0°C for 15 min. Methyl iodide (0.26g, 1.37 mmol) was added to the reaction mixture at 0°C. The reaction mixture was stirred at rt for 1 h, poured into ice cold water (20 ml) and extracted with EtOAc (2 x 15 ml). The organic layer was washed with brine (20 ml). The organic phase was collected, dried over Na2SC>4, filtered and concentrated under reduced pressure yielding tert-butyl (4-bromopyridin-2-yl)(methyl)carbamate (0.25g, 0.87 mmol). This material was directly used for the next step without further purification. LCMS: Method A, 2.50 min, MS: ES+ 230.9; 232.9 (M-56)

Reference: [1] Patent: WO2008/57497, 2008, A2, . Location in patent: Page/Page column 296-297
[2] Patent: WO2007/89669, 2007, A2, . Location in patent: Page/Page column 208
[3] Patent: WO2008/57469, 2008, A1, . Location in patent: Page/Page column 296-297
[4] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 296-297
[5] Patent: WO2016/46530, 2016, A1, . Location in patent: Page/Page column 79
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