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[ CAS No. 56341-41-4 ] {[proInfo.proName]}

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Chemical Structure| 56341-41-4
Chemical Structure| 56341-41-4
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Product Details of [ 56341-41-4 ]

CAS No. :56341-41-4 MDL No. :MFCD02179598
Formula : C8H6FNO Boiling Point : -
Linear Structure Formula :- InChI Key :DDIIYGHHUMKDGI-UHFFFAOYSA-N
M.W : 151.14 Pubchem ID :3731012
Synonyms :
Chemical Name :5-Fluoroindolin-2-one

Calculated chemistry of [ 56341-41-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.69
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.5
Log Po/w (XLOGP3) : 1.26
Log Po/w (WLOGP) : 1.17
Log Po/w (MLOGP) : 1.56
Log Po/w (SILICOS-IT) : 2.27
Consensus Log Po/w : 1.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.97
Solubility : 1.6 mg/ml ; 0.0106 mol/l
Class : Very soluble
Log S (Ali) : -1.47
Solubility : 5.12 mg/ml ; 0.0339 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.15
Solubility : 0.107 mg/ml ; 0.000708 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

Safety of [ 56341-41-4 ]

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

Application In Synthesis of [ 56341-41-4 ]

* 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 [ 56341-41-4 ]
  • Downstream synthetic route of [ 56341-41-4 ]

[ 56341-41-4 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 56341-41-4 ]
  • [ 443-69-6 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 26, p. 4671 - 4673
[2] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6385 - 6388
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  • [ 443-69-6 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 59, p. 8265 - 8268
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  • [ 443-69-6 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 59, p. 8265 - 8268
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  • [ 253870-02-9 ]
  • [ 56341-41-4 ]
  • [ 356068-93-4 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: for 5 h; Reflux
(NH4)2SO4 (0.09 g, 0.67 mmol) was added into a stirred mixture of 8 (1.0 g, 6.61 mmol) in HMDS (20 mL, 20 P) at room temperature.
The reaction mixture was then heated to reflux and maintained at that temperature for no less than 5 hours.
Monitor the reaction by GC.
After the reaction is completed, 14 (1.1 g, 3.77 mmol) and TMSOTf (0.29 g, 1.32 mmol) were added.
Then the mixture was stirred, once the reaction was complete (as indicated by HPLC analysis) it was quenched with water (6 mL, 6 P.) and MeCN (30 mL).
The mixture was filtrated and the filtrate cake was washed with MeCN (20 mL) and EtOH (5 mL), then it was dried under vacuum at 40° C. overnight to give the goal product 15 (1.92 g, 97percent yield) as a yellow to brown powder with about 82.1percent HPLC purity.
96% for 3 h; Heating / reflux A mixture of 5-fluoro-1 , 3-dihydroindol-2-one (1.62 g, 10.2 mmol), 5- formyl^λ-dimethyl-IH-pyrrole-S-carboxylic acid (1.96 g, 10.7 mmol), pyrrolidine (12 drops) and absolute ethanol was heated to reflux for 3 hours. The mixture was cooled to 25 0C and the solids were collected by filtration. The solids were stirred with ethanol (30 mL) at 72 °C for 30min. The mixture was cooled to 25 0C and the solids were collected again by filtration, washed with ethanol (6 mL), and dried under vacuum overnight to give an orange solid (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3- carboxylic acid (3.094 g, 96percent). LC-ESIMS observed [M+H]+ 301 (calculated for Ci6Hi3FN2O3 300.09).
96% With pyrrolidine In ethanol for 3 h; Heating / reflux Exemplary Chiral Species; A general scheme for synthesizing chiral species of the invention is outline below:; Step 1 :; A mixture of 5-fluoro-1 , 3-dihydroindol-2-one (1.62 g, 10.2 mmol), 5- formyl^^-dimethyl-I H-pyrrole-S-carboxylic acid (1.96 g, 10.7 mmol), pyrrolidine (12 drops) and absolute ethanol was heated to reflux for 3 hours. The mixture was cooled to 25 0C and the solids were collected by filtration. The solids were stirred with ethanol (30 ml.) at 72 0C for 30min. The mixture was cooled to 25 0C and the solids were collected again by filtration, washed with ethanol (6 ml_), and dried under vacuum overnight to give an orange solid (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1 H-pyrrole-3- carboxylic acid (3.094 g, 96percent). LC-ESIMS observed [M+H]+ 300.95 (calculated for Ci6Hi3FN2O3 300.09).
93% With pyrrolidine In ethanol for 3 h; Heating / reflux Step 1 : A mixture of 5-fluoro-l,3-dihydroindol-2-one (A2) (2Og, 132mmol), 5-formyl-2,4-dimethylpyrrole-3-carboxylic acid (Al) (21. Ig, 126mmol), pyrrolidine (5ml) and absolute ethanol (40OmL) were heated to reflux for 3 hours. Then the mixture was cooled to room temperature and the solid was collected by filtration, washed with ethanol (10OmL). The solid was stirred in ethanol (350ml) at reflux for 0.5h again. The mixture was cooled to room temperature and the solid was collected by filtration, washed with ethanol (100ml) and dried under vacuum overnight to give (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-lH-pyrrole-3- carboxylic acid (A3) (35.3g, 93percent) as orange solid. LC-MS observed [M-H]+: 299.2.
93% With pyrrolidine In ethanol for 3 h; Heating / reflux EXAMPLES The general procedure for the preparation of many examples is shown below: Step 1: A mixture of 5-fluoro-1,3-dihydroindol-2-one (A2) (20 g, 132 mmol), 5-formyl-2,4-dimethylpyrrole-3-carboxylic acid (A1) (21.1 g, 126 mmol), pyrrolidine (5 ml) and absolute ethanol (400 mL) were heated to reflux for 3 hours. Then the mixture was cooled to room temperature and the solid was collected by filtration, washed with ethanol (100 mL). The solid was stirred in ethanol (350 ml) at reflux for 0.5 h again. The mixture was cooled to room temperature and the solid was collected by filtration, washed with ethanol (100 ml) and dried under vacuum overnight to give (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (A3) (35.3 g, 93percent) as orange solid. LC-MS observed [M-H+: 299.2.
91%
Stage #1: With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 5 h; Reflux
Stage #2: With 5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 45℃; for 0.25 h;
Stage #3: With trimethylsilyl trifluoromethanesulfonate In acetonitrile
(NH4)2SO4 (0.05 g, 0.38 mmol) was added into a stirred mixture of 8 (0.57 g, 3.77 mmol) in HMDS (7.1 mL, 12.5 P.) at room temperature.
The reaction mixture was then heated to reflux and maintained at that temperature for no less than 5 hours.
Monitor the reaction by GC.
After the reaction is completed, the reaction was distilled to remove about half of HMDS to give 20 of about 90percent GC purity.
To the solution of 20 in HMDS (about 3.5 mL, 6.25 P.) at 45° C. was added MeCN (30 mL, 52.6 P.).
After stirring for 15 minutes, 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (14; 0.63 g, 3.77 mmol) and TMSOTf (0.16 g, 0.72 mmol) were added.
Then the mixture was stirred for more than 4 hours, once the reaction was complete (as indicated by HPLC analysis) it was quenched with water (3 mL, 5 P.).
The mixture was filtered and the filtrate cake was washed with Ethanol (5 mL), then it was dried under vacuum at 40° C. overnight to give the goal product 15 (1.03 g, 91percent yield) as a yellow to brown powder with about 85percent HPLC purity. 1H NMR (300 MHz, d6-DMSO): δ 2.48 (m, 6H, H-20, 21), 6.83 (m, 1H, H-6), 6.85 (m, 1H, H-4), 7.71 (m, 1H, H-12), 7.73 (m, 1H, H-1), 10.98 (s, 1H, H-7), 13.95 (s, 1H, H-14). API-ESI (NEG): m/z 299.0
79%
Stage #1: With pyrrolidine In ethanol for 4.5 h; Heating / reflux
Stage #2: With acetic acid In ethanol for 0.5 h; Heating / reflux
Stage #3: With hydrogenchloride In water; acetone for 2.16667 h;
5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (61 g), 5-fluoro-1,3-dihydro-indol-2-one (79 g), ethanol (300 ml) and pyrrolidine (32 ml) were refluxed for 4.5 hours. Acetic acid (24 ml) was added to the mixture and refluxing was continued for 30 minutes. The mixture was cooled to room temperature and the solids collected by vacuum filtration and washed twice with ethanol. The solids were stirred for 130 minutes in 40 percent acetone in water (400 ml) containing 12 N hydrochloric acid (6.5 ml). The solids were collected by vacuum filtration and washed twice with 40 percent acetone in water. The solids were dried under vacuum to give 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (86 g, 79 percent yield) as an orange solid. 1H-NMR (dimethylsulfoxide-d6) δ 2.48, 2.50 (2xs, 6H, 2xCH3), 6.80, 6.88, 7.68, 7.72 (4xm, 4H, aromatic and vinyl), 10.88 (s, 1H, CONH), 12.12 (s, 1H, COOH), 13.82 (s, 1H, pyrrole NH). MS m/z 299 [M-1].
79%
Stage #1: With pyrrolidine In ethanol for 4.5 h; Heating / reflux
Stage #2: With acetic acid In ethanol for 0.5 h; Heating / reflux
5-Formyl-2,4-dimethyl-lH-pyrrole-3-carboxylic acid (61 g), 5-fluoro-l,3-dihydro-indol-2-one (79 g), ethanol (300 mL) and pyrrolidine (32 mL) were refluxed for 4.5 hours. Acetic acid (24 mL) was added to the mixture and refluxing was continued for 30 minutes. The mixture was cooled to room temperature and the solids collected by vacuum filtration and washed twice with ethanol. The solids were stirred for 130 minutes in 40percent acetone in water (400 mL) containing 12 N hydrochloric acid (6.5mL). The solids were collected by vacuum filtration and washed twice with 40percent acetone in water. The solids were dried under vacuum to give 5-[5-fluoro-2-oxo- 1 ,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl- lH-pyrrole-3- carboxylic acid (86 g, 79percent yield) as an orange solid.
77% With pyrrolidine In ethanol at 78℃; for 6 h; Step Ig. 5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl)-N-hydroxy-2,4-dimethyl- lH-pyrrole-3-carboxamide (compound 1)A mixture of compound 108 (4.0 g. 24 mmol), 102 (3.6 g 24 mmol) and pyrrolidine (2 mL) in ethanol (200 mL) was stirred and heated at 78°C for 6h. The mixture was filtered to give yellow solid, dried to yield product 1 (5.5g, 77percent). LCMS: m/z 301(M+l), 1H NMR(DMSO-^6) δ2.39 (s, 3H), 2.42 (s, 3H), 6.82 ( m, 2H), 7.77 (s, IH), 7.80 (m, IH), 10.93 (s, IH), 12.23 (s, IH), 13.86 (s, IH).
77% at 78℃; for 6 h; A mixture of compound 108 (4.0 g. 24 mmol), 102 (3.6 g 24 mmol) and pyrrolidine (2 mL) in ethanol (200 mL) was stirred and heated at 780C for 6h. The mixture was filtered to give yellow solid, dried to yield product 1 (5.5g, 77percent). LCMS: m/z 301(M+l), 1H NMR(DMSO-J6) δ2.39 (s, 3H), 2.42 (s, 3H), 6.82 ( m, 2H), 7.77 (s, IH), 7.80 (m, IH), 10.93 (s, IH), 12.23 (s, IH), 13.86 (s, IH).

Reference: [1] Patent: US2013/190512, 2013, A1, . Location in patent: Paragraph 0088
[2] Patent: WO2007/81560, 2007, A2, . Location in patent: Page/Page column 6
[3] Patent: WO2006/127961, 2006, A1, . Location in patent: Page/Page column 15-16
[4] Patent: WO2008/33562, 2008, A2, . Location in patent: Page/Page column 34
[5] Patent: US2009/76005, 2009, A1, . Location in patent: Page/Page column 12; 13
[6] Patent: US2013/190512, 2013, A1, . Location in patent: Paragraph 0086
[7] Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 248 - 262
[8] Patent: WO2004/76410, 2004, A2, . Location in patent: Page 11-12
[9] Patent: WO2007/34272, 2007, A1, . Location in patent: Page/Page column 17
[10] Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 2018, vol. 1092, p. 515 - 523
[11] Patent: WO2008/33743, 2008, A1, . Location in patent: Page/Page column 53; 57
[12] Patent: WO2008/33747, 2008, A2, . Location in patent: Page/Page column 202
[13] Journal of Medicinal Chemistry, 2003, vol. 46, # 7, p. 1116 - 1119
[14] Patent: WO2011/110199, 2011, A1, . Location in patent: Page/Page column 15
[15] Patent: WO2012/58780, 2012, A1, . Location in patent: Page/Page column 33-34
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YieldReaction ConditionsOperation in experiment
79% With hydrogenchloride; acetic acid In ethanol; water; acetone Scale-Up Procedure:
5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (61 g), 5-fluoro-1,3-dihydro-indol-2-one (79 g), ethanol (300 mL) and pyrrolidine (32 mL) were refluxed for 4.5 hours.
Acetic acid (24 mL) was added to the mixture and refluxing was continued for 30 minutes.
The mixture was cooled to room temperature and the solids collected by vacuum filtration and washed twice with ethanol.
The solids were stirred for 130 minutes in 40percent acetone in water (400 mL) containing 12 N hydrochloric acid (6.5 mL).
The solids were collected by vacuum filtration and washed twice with 40percent acetone in water.
The solids were dried under vacuum to give 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (86 g, 79percent yield) as an orange solid. 1H-NMR (dimethylsulfoxide-d6) δ 2.48, 2.50 (2*s, 6H, 2*CH3), 6.80, 6.88, 7.68, 7.72 (4*m, 4H, aromatic and vinyl), 10.88 (s, 1H, CONH), 12.12 (s, 1H, COOH), 13.82 (s, 1H, pyrrole NH). MS m/z 299 [M-1].
79% With hydrogenchloride; acetic acid In ethanol; water; acetone Scale-Up Procedure:
5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (61 g), 5-fluoro-1,3-dihydro-indol-2-one (79 g), ethanol (300 mL) and pyrrolidine (32 mL) were refluxed for 4.5 hours.
Acetic acid (24 mL) was added to the mixture and refluxing was continued for 30 minutes.
The mixture was cooled to room temperature and the solids collected by vacuum filtration and washed twice with ethanol.
The solids were stirred for 130 minutes in 40percent acetone in water (400 mL) containing 12 N hydrochloric acid (6.5 mL).
The solids were collected by vacuum filtration and washed twice with 40percent acetone in water.
The solids were dried under vacuum to give 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (86 g, 79percent yield) as an orange solid. 1H-NMR (dimethylsulfoxide-d6) δ 2.48, 2.50 (2*s, 6H, 2*CH3), 6.80, 6.88, 7.68, 7.72 (4*m, 4H, aromatic and vinyl), 10.88 (s, 1H, CONH), 12.12 (s, 1H, COOH), 13.82 (s, 1H, pyrrole NH).
MS m/z 299 [M-1].
79% With hydrogenchloride; acetic acid In ethanol; water; acetone Scale-up procedure:
5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (61 g), 5-fluoro-1,3-dihydro-indol-2-one (79 g), ethanol (300 mL) and pyrrolidine (32 mL) were refluxed for 4.5 hours.
Acetic acid (24 mL) was added to the mixture and refluxing was continued for 30 minutes.
The mixture was cooled to room temperature and the solids collected by vacuum filtration and washed twice with ethanol.
The solids were stirred for 130 minutes in 40percent acetone in water (400 mL) containing 12 N hydrochloric acid (6.5 mL).
The solids were collected by vacuum filtration and washed twice with 40percent acetone in water.
The solids were dried under vacuum to give 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (86 g, 79percent yield) as an orange solid. 1H-NMR (dimethylsulfoxide-d6) δ 2.48, 2.50 (2*s, 6H, 2*CH3), 6.80, 6.88, 7.68, 7.72 (4*m, 4H, aromatic and vinyl), 10.88 (s, 1H, CONH), 12.12 (s, 1H, COOH), 13.82 (s, 1H, pyrrole NH). MS m/z 299 [M-1].
Reference: [1] Patent: US2003/216410, 2003, A1,
[2] Patent: US2003/100555, 2003, A1,
[3] Patent: US2002/156292, 2002, A1,
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  • [ 356068-93-4 ]
Reference: [1] Patent: US2003/92917, 2003, A1,
[2] Patent: US2004/209937, 2004, A1,
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  • [ 356068-93-4 ]
Reference: [1] Patent: WO2012/58780, 2012, A1,
[2] Patent: US2013/190512, 2013, A1,
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  • [ 356068-94-5 ]
Reference: [1] Patent: WO2004/76410, 2004, A2, . Location in patent: Page 11
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  • [ 56341-41-4 ]
  • [ 118753-70-1 ]
  • [ 866028-06-0 ]
YieldReaction ConditionsOperation in experiment
15%
Stage #1: With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.75 h;
Stage #2: at -78℃; for 19 h;
tert-Butyl 5-fluoro-2-oxo-1, 2-dihvdro-1'H spiro [indole-3, 4'-piperidinel-1'- carboxylate To a stirred solution of 5-fluoro-1, 3-dihydro-2H-indol-2-one (1.80 g, 11.9 mmol) in tetrahydrofuran (30 mL) was added dropwise a 1 M solution of sodium bis (trimethylsilyl) amide in tetrahydrofuran (35.7 mL, 35.7 mmol) at-78 °C for 15 min and the mixture was stirred for 1.5 h at the same temperature. To the mixture was added dropwise a solution of tert-butyl bis (2-chloroethyl) carbamate (2.88 g, 11.9 mmol) in tetrahydrofuran (10 mL) at-78 °C, then this resulting mixture was slowly warmed up to room temperature and stirred for 19 h at the same temperature. The reaction mixture was quenched by the addition of ammonium chloride aqueous solution, and concentrated to give a brown residue. The crude material was partitioned between ethyl acetate and water, and then the organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/acetone (3/1) to afford 356 mg (15percent) of the title compound as a slight brown syrup: 'H-NMR (CDC13) 8 8.56 (1H, br. s), 7.03-6. 83 (3H, m), 3.89-3. 69 (4H, m), 1.92-1. 72 (4H, m), 1.50 (9H, s); MS (ESI) 319 (M-H)-.
7%
Stage #1: at -78℃; for 1 h;
Stage #2: at -50℃; Reflux
5-fluoroindolin-2-one 5a (35 g, 231.576 mmol, 1 eq.) was added to a solution of LiHMDS (700 ml, 700 mmol, 3 eq) at -78°C. The mixture was stirred 1 hour at -78°C, then tert-butyl bis(2-chloroethyl)carbamate 5b (5 6.075 g, 231.576 mmol, 1 eq) wasadded, maintaining the internal temperature <-5 0°C. The reaction was then warmed to ambient temperature during 2 hours, and the reaction was refluxed overnight. The mixture was quenched with H20 and the mixture was partitioned between EtOAc and H20.The aqueous solution was extracted with EtOAc and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuum. Theresulting residue was purified by high performance liquid chromatography (HPLC condition: Column: Synergi-10im, 250x50mm1.D, Flow rate: 80 ml/min, Mobile Phase A: Purified water (containing 0. 1percentTFA), Mobile Phase B: Acetonitrile, Gradient: 35- 65 percent( percentB)) to give 5.003 g (7percent yield) of tert-butyl 5-fluoro-2-oxospiro[indoline-3,4’- piperidine]- 1 ‘-carboxylate 5c.
Reference: [1] Patent: WO2005/92858, 2005, A2, . Location in patent: Page/Page column 60
[2] Patent: WO2014/60411, 2014, A1, . Location in patent: Page/Page column 40
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YieldReaction ConditionsOperation in experiment
62.5% at -5 - 20℃; 5-Fluoro-1,3-dihydro-indol-2-one (5.0 g, 33 mmol) was added with 98percent sulfuric acid (17.6 ml) and 65percent-68percent nitric acid (2.1 ml) in an ice-water bath with salt at -5° C. Upon the completion of the addition, the mixture was stirred for 1 hour at room temperature and added with ice-water until precipitate was formed. The solid was filtered and washed with water (50 ml.x.3) and recrystallized from acetic acid and water to give 7-amino-5-fluoro-1,3-dihydro-indol-2-one (4.0 g, 62.5percent) as an orange solid.MS m/z (ESI): 196 [M+1]
Reference: [1] Patent: US2010/4239, 2010, A1, . Location in patent: Page/Page column 56-57
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