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[ CAS No. 885520-70-7 ]

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2D
Chemical Structure| 885520-70-7
Chemical Structure| 885520-70-7
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Product Details of [ 885520-70-7 ]

CAS No. :885520-70-7MDL No. :MFCD08272203
Formula :C8H5BrFNBoiling Point :-
Linear Structure Formula :-InChI Key :N/A
M.W :214.03Pubchem ID :24728173
Synonyms :

Computed Properties of [ 885520-70-7 ]

TPSA : 15.8 H-Bond Acceptor Count : 1
XLogP3 : 2.8 H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 885520-70-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 885520-70-7 ]

  • Upstream synthesis route of [ 885520-70-7 ]
  • Downstream synthetic route of [ 885520-70-7 ]

[ 885520-70-7 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 1093066-65-9 ]
  • [ 885520-70-7 ]
YieldReaction ConditionsOperation in experiment
37% With hydrazine In tetrahydrofuran; methanol; water at 20℃; for 5.00 h; To a suspension of the pyrrolidine (10.0 g, 31.7 mmol) and Raney.(R).-Nickel (suspension in H20, 15 mL) in MeOH:THF (1:1, 150 mL) was added hydrazine monohydrate (2.3 mL, 47.4 mmol) at 0 0C and the mixture stirred at RT for 5 hours. The reaction mixture was then filtered through Celite and the filter cake washed with EtOAc. The filtrate was evaporated to dryness and the resulting residue to give the title compound as pale oil (2.57 g, 37 percent). NMR δH (300 MHz, CDCl3) 6.57 (apparent t, J = 2.7, IH), 7.04 (dd, J = 2.1, 9.1, IH), 7.12 (dd, J = 2.1, 9.1, IH), 7.20-7.25 (m, IH) and 8.25 (s, IH).
37% With hydrazine In tetrahydrofuran; methanol; water at 0 - 20℃; for 5.00 h; Reference Example 44-Bromo-6-fluoro-lH-indoleTo a solution of l-bromo-5-fluoro-2-methyl-3-nitro-benzene (7.49 g, 31.8 mmol) in dioxane (40 mL) was added DMF-DMA (21.0 mL, 158 mmol) and pyrrolidine (2.6 mL, 31.1 mmol). The reaction mixture was heated at 100 °C. The mixture was cooled to RT and evaporated to dryness to give l-[2-(2-bromo-4-fluoro-6-nitro-phenyl)-l -methyl vinyl]- pyrrolidine as a dark red residue (10.0 g, theoretical yield). To a suspension of the pyrrolidine (10.0 g, 31.7 mmol) and Raney.(R).-Nickel (suspension in H2O, 15 mL) in MeOH:THF (1:1, 150 mL) was added hydrazine monohydrate (2.3 mL, 47.4 mmol) at 0 0C and the mixture stirred at RT for 5 hours. The reaction mixture was then filtered through Celite and the filter cake washed with EtOAc. The filtrate was evaporated to dryness and the resulting residue to give the title compound as pale oil (2.57 g, 37 percent).NMR δH (300 MHz, CDCl3) 6.57 (apparent t, J = 2.7, IH), 7.04 (dd, J = 2.1, 9.1, IH), 7.12 (dd, J = 2.1, 9.1, IH), 7.20-7.25 (m, IH) and 8.25 (s, IH).
Reference: [1] Patent: WO2008/152387, 2008, A1. Location in patent: Page/Page column 34
[2] Patent: WO2009/53716, 2009, A1. Location in patent: Page/Page column 56
[3] Patent: WO2008/152394, 2008, A1. Location in patent: Page/Page column 39
[4] Patent: WO2008/152390, 2008, A1. Location in patent: Page/Page column 54-55
  • 2
  • [ 4637-24-5 ]
  • [ 502496-33-5 ]
  • [ 885520-70-7 ]
YieldReaction ConditionsOperation in experiment
39%
Stage #1: at 20℃; Heating / reflux
Stage #2: With iron; acetic acid In N,N-dimethyl-formamide for 0.67 h; Heating / reflux
Stage #3: With water; sodium carbonate In dichloromethane
Intermediate 35; 4-Bromo-6-fluoro-lH-indole; l-Bromo-5-fluoro-2-methyl-3-nitrobenzene (2.00 g, 8.55 mmol) and(dimethoxymethyl)dimethylamine (5.66 mL, 42.7 mmol) in dry DMF (20 mL) was refiuxed under N2 for 8 h, then rt. over night. The mixture was diluted with DCM and extracted 5 times with water. The organic layer was dried, filtered and concentrated under reduced pressure. The residue was dissolved in AcOH (10 mL) and added drop wise to a boiling mixture of Fe(s, fine powder) in AcOH (10 mL). The mixture was refiuxed for 40 min., partitioned between DCM and saturated aq. Na2CO3/brine (the mixture was filtered through celite before phase separation). The water layer was extracted once more with DCM. The organic layers were combined, dried and concentrated. Purification was performed by flash column chromatography (DCM/hexane 1:3) and afforded the title compound (660 mg, 39percent) as a yellow oil. MS (ESI+) for C8H5BrFN m/z 214 (M+H)+.
27%
Stage #1: With pyrrolidine In 1,4-dioxane at 20 - 100℃; for 18.00 h;
Stage #2: With iron; acetic acid In 1,4-dioxane for 1.00 h; Reflux
Example 41 N4-(5-Cyclobutyl- 1 H-pyrazol-3-yl)-N2-((6-fluoro- 1 H-indol-4-yl)methyl)pyrimidine-2,4-diamine Formate (1-88) step 1 : To a solution of l-bromo-5-fluoro-2-methyl-3-nitrobenzene (4.69 g, 20 mmol) in 1,4-dioxane (25 mL) at RT was slowly added DMF dimethylacetal (13.3 mL) and pyrrolidine (1.7 mL). The solution was heated at 100 °C for 18 h, then concentrated in vacuo to give a dark residue. To the residue was added HOAc (30 mL) and iron powder (11 g, 200 mmol) then the mixture was heated to reflux for 1 h, cooled to RT, neutralized by addition of 50percent aq. NaOH and extracted with EtOAc (2 x 200 mL). The combined organic extracts were dried (MgSO i), filtered and concentrated in vacuo. The residue was purified by Si02 chromatography eluting with an EtO Ac/petroleum ether gradient (5 to 30percent EtOAc) to afford 1.16 g (27percent) of 4-bromo-6-fluoro-lH-indole (224) -as brown solid: MS (ESI) m/z = 213.9 [M+l] +.
Reference: [1] Patent: WO2008/3703, 2008, A1. Location in patent: Page/Page column 91
[2] Patent: WO2013/26914, 2013, A1. Location in patent: Page/Page column 158
  • 3
  • [ 1181566-93-7 ]
  • [ 885520-70-7 ]
Reference: [1] Patent: WO2009/103710, 2009, A1. Location in patent: Page/Page column 21
  • 4
  • [ 1354219-92-3 ]
  • [ 885520-70-7 ]
YieldReaction ConditionsOperation in experiment
800 mg at 110℃; for 1.50 h; An acetic acid (20 ml) solution containing the deep brown oily matter obtained in the 2nd step was added to amixture of iron powder (3.61 g) and acetic acid (20 ml) at 110°C for 30 minutes. The resulting mixture was stirred for 1hour and then diluted with ethyl acetate. Insoluble matter was removed by filtration with Celite, the filtrate was washedwith water and 1M hydrochloric acid (x3). The obtained organic layer was poured into a saturated aqueous sodiumhydrogen carbonate solution to separate the organic layer, and the organic layer was washed with water and saturated saline and dried over anhydrous sodium sulfate. Thereafter, activated carbon was added and insoluble matter wasremoved by filtration with Celite. The solvent was distilled away under reduced pressure, and light brown oily matter of4-bromo-6-fluoro-1H-indole (880 mg) was thus obtained.MS (ESI m/z): 214, 216 (M+H)RT (min): 1.561H-NMR (DMSO-d6, 300MHz) δ:11.53 (br, 1H), 7.46 (t, 1H, J = 3.0Hz), 7.24 (dd, 1H, J = 5.6, 3.0 Hz), 7.19 (dd, 1H, J =9.2, 2.0Hz), 6.39 (d, 1H, J = 2.0Hz)
Reference: [1] Patent: EP2589592, 2018, B1. Location in patent: Paragraph 0755; 0758
[2] Patent: WO2007/122410, 2007, A1. Location in patent: Page/Page column 67
  • 5
  • [ 502496-33-5 ]
  • [ 885520-70-7 ]
Reference: [1] Patent: EP2589592, 2018, B1
[2] Patent: WO2007/122410, 2007, A1
[3] Patent: WO2007/122410, 2007, A1
[4] Patent: WO2008/152394, 2008, A1
[5] Patent: WO2008/152390, 2008, A1
[6] Patent: WO2009/103710, 2009, A1
  • 6
  • [ 446-10-6 ]
  • [ 885520-70-7 ]
Reference: [1] Patent: EP2589592, 2018, B1
[2] Patent: WO2007/122410, 2007, A1
[3] Patent: WO2007/122410, 2007, A1
[4] Patent: WO2008/152394, 2008, A1
[5] Patent: WO2008/152390, 2008, A1
  • 7
  • [ 1057369-11-5 ]
  • [ 885520-70-7 ]
Reference: [1] Patent: WO2007/122410, 2007, A1. Location in patent: Page/Page column 105
  • 8
  • [ 1093066-65-9 ]
  • [ 885520-70-7 ]
YieldReaction ConditionsOperation in experiment
37% With hydrazine In tetrahydrofuran; methanol; water at 20℃; for 5.00 h; To a suspension of the pyrrolidine (10.0 g, 31.7 mmol) and Raney.(R).-Nickel (suspension in H20, 15 mL) in MeOH:THF (1:1, 150 mL) was added hydrazine monohydrate (2.3 mL, 47.4 mmol) at 0 0C and the mixture stirred at RT for 5 hours. The reaction mixture was then filtered through Celite and the filter cake washed with EtOAc. The filtrate was evaporated to dryness and the resulting residue to give the title compound as pale oil (2.57 g, 37 percent). NMR δH (300 MHz, CDCl3) 6.57 (apparent t, J = 2.7, IH), 7.04 (dd, J = 2.1, 9.1, IH), 7.12 (dd, J = 2.1, 9.1, IH), 7.20-7.25 (m, IH) and 8.25 (s, IH).
37% With hydrazine In tetrahydrofuran; methanol; water at 0 - 20℃; for 5.00 h; Reference Example 44-Bromo-6-fluoro-lH-indoleTo a solution of l-bromo-5-fluoro-2-methyl-3-nitro-benzene (7.49 g, 31.8 mmol) in dioxane (40 mL) was added DMF-DMA (21.0 mL, 158 mmol) and pyrrolidine (2.6 mL, 31.1 mmol). The reaction mixture was heated at 100 °C. The mixture was cooled to RT and evaporated to dryness to give l-[2-(2-bromo-4-fluoro-6-nitro-phenyl)-l -methyl vinyl]- pyrrolidine as a dark red residue (10.0 g, theoretical yield). To a suspension of the pyrrolidine (10.0 g, 31.7 mmol) and Raney.(R).-Nickel (suspension in H2O, 15 mL) in MeOH:THF (1:1, 150 mL) was added hydrazine monohydrate (2.3 mL, 47.4 mmol) at 0 0C and the mixture stirred at RT for 5 hours. The reaction mixture was then filtered through Celite and the filter cake washed with EtOAc. The filtrate was evaporated to dryness and the resulting residue to give the title compound as pale oil (2.57 g, 37 percent).NMR δH (300 MHz, CDCl3) 6.57 (apparent t, J = 2.7, IH), 7.04 (dd, J = 2.1, 9.1, IH), 7.12 (dd, J = 2.1, 9.1, IH), 7.20-7.25 (m, IH) and 8.25 (s, IH).
Reference: [1] Patent: WO2008/152387, 2008, A1. Location in patent: Page/Page column 34
[2] Patent: WO2009/53716, 2009, A1. Location in patent: Page/Page column 56
[3] Patent: WO2008/152394, 2008, A1. Location in patent: Page/Page column 39
[4] Patent: WO2008/152390, 2008, A1. Location in patent: Page/Page column 54-55
  • 9
  • [ 4637-24-5 ]
  • [ 502496-33-5 ]
  • [ 885520-70-7 ]
YieldReaction ConditionsOperation in experiment
39%
Stage #1: at 20℃; Heating / reflux
Stage #2: With iron; acetic acid In N,N-dimethyl-formamide for 0.67 h; Heating / reflux
Stage #3: With water; sodium carbonate In dichloromethane
Intermediate 35; 4-Bromo-6-fluoro-lH-indole; l-Bromo-5-fluoro-2-methyl-3-nitrobenzene (2.00 g, 8.55 mmol) and(dimethoxymethyl)dimethylamine (5.66 mL, 42.7 mmol) in dry DMF (20 mL) was refiuxed under N2 for 8 h, then rt. over night. The mixture was diluted with DCM and extracted 5 times with water. The organic layer was dried, filtered and concentrated under reduced pressure. The residue was dissolved in AcOH (10 mL) and added drop wise to a boiling mixture of Fe(s, fine powder) in AcOH (10 mL). The mixture was refiuxed for 40 min., partitioned between DCM and saturated aq. Na2CO3/brine (the mixture was filtered through celite before phase separation). The water layer was extracted once more with DCM. The organic layers were combined, dried and concentrated. Purification was performed by flash column chromatography (DCM/hexane 1:3) and afforded the title compound (660 mg, 39percent) as a yellow oil. MS (ESI+) for C8H5BrFN m/z 214 (M+H)+.
27%
Stage #1: With pyrrolidine In 1,4-dioxane at 20 - 100℃; for 18.00 h;
Stage #2: With iron; acetic acid In 1,4-dioxane for 1.00 h; Reflux
Example 41 N4-(5-Cyclobutyl- 1 H-pyrazol-3-yl)-N2-((6-fluoro- 1 H-indol-4-yl)methyl)pyrimidine-2,4-diamine Formate (1-88) step 1 : To a solution of l-bromo-5-fluoro-2-methyl-3-nitrobenzene (4.69 g, 20 mmol) in 1,4-dioxane (25 mL) at RT was slowly added DMF dimethylacetal (13.3 mL) and pyrrolidine (1.7 mL). The solution was heated at 100 °C for 18 h, then concentrated in vacuo to give a dark residue. To the residue was added HOAc (30 mL) and iron powder (11 g, 200 mmol) then the mixture was heated to reflux for 1 h, cooled to RT, neutralized by addition of 50percent aq. NaOH and extracted with EtOAc (2 x 200 mL). The combined organic extracts were dried (MgSO i), filtered and concentrated in vacuo. The residue was purified by Si02 chromatography eluting with an EtO Ac/petroleum ether gradient (5 to 30percent EtOAc) to afford 1.16 g (27percent) of 4-bromo-6-fluoro-lH-indole (224) -as brown solid: MS (ESI) m/z = 213.9 [M+l] +.
Reference: [1] Patent: WO2008/3703, 2008, A1. Location in patent: Page/Page column 91
[2] Patent: WO2013/26914, 2013, A1. Location in patent: Page/Page column 158
  • 10
  • [ 1181566-93-7 ]
  • [ 885520-70-7 ]
Reference: [1] Patent: WO2009/103710, 2009, A1. Location in patent: Page/Page column 21
  • 11
  • [ 1354219-92-3 ]
  • [ 885520-70-7 ]
YieldReaction ConditionsOperation in experiment
800 mg at 110℃; for 1.50 h; An acetic acid (20 ml) solution containing the deep brown oily matter obtained in the 2nd step was added to amixture of iron powder (3.61 g) and acetic acid (20 ml) at 110°C for 30 minutes. The resulting mixture was stirred for 1hour and then diluted with ethyl acetate. Insoluble matter was removed by filtration with Celite, the filtrate was washedwith water and 1M hydrochloric acid (x3). The obtained organic layer was poured into a saturated aqueous sodiumhydrogen carbonate solution to separate the organic layer, and the organic layer was washed with water and saturated saline and dried over anhydrous sodium sulfate. Thereafter, activated carbon was added and insoluble matter wasremoved by filtration with Celite. The solvent was distilled away under reduced pressure, and light brown oily matter of4-bromo-6-fluoro-1H-indole (880 mg) was thus obtained.MS (ESI m/z): 214, 216 (M+H)RT (min): 1.561H-NMR (DMSO-d6, 300MHz) δ:11.53 (br, 1H), 7.46 (t, 1H, J = 3.0Hz), 7.24 (dd, 1H, J = 5.6, 3.0 Hz), 7.19 (dd, 1H, J =9.2, 2.0Hz), 6.39 (d, 1H, J = 2.0Hz)
Reference: [1] Patent: EP2589592, 2018, B1. Location in patent: Paragraph 0755; 0758
[2] Patent: WO2007/122410, 2007, A1. Location in patent: Page/Page column 67
  • 12
  • [ 502496-33-5 ]
  • [ 885520-70-7 ]
Reference: [1] Patent: EP2589592, 2018, B1
[2] Patent: WO2007/122410, 2007, A1
[3] Patent: WO2007/122410, 2007, A1
[4] Patent: WO2008/152394, 2008, A1
[5] Patent: WO2008/152390, 2008, A1
[6] Patent: WO2009/103710, 2009, A1
  • 13
  • [ 446-10-6 ]
  • [ 885520-70-7 ]
Reference: [1] Patent: EP2589592, 2018, B1
[2] Patent: WO2007/122410, 2007, A1
[3] Patent: WO2007/122410, 2007, A1
[4] Patent: WO2008/152394, 2008, A1
[5] Patent: WO2008/152390, 2008, A1
  • 14
  • [ 1057369-11-5 ]
  • [ 885520-70-7 ]
Reference: [1] Patent: WO2007/122410, 2007, A1. Location in patent: Page/Page column 105
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