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[ CAS No. 146137-76-0 ]

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2D
Chemical Structure| 146137-76-0
Chemical Structure| 146137-76-0
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Product Details of [ 146137-76-0 ]

CAS No. :146137-76-0MDL No. :MFCD03093999
Formula : C7H4FIO Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :250.01Pubchem ID :-
Synonyms :

Computed Properties of [ 146137-76-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 146137-76-0 ]

Signal Word:DangerClass:6.1
Precautionary Statements:P261-P301+P310-P305+P351+P338UN#:2811
Hazard Statements:H301-H315-H319-H335Packing Group:
GHS Pictogram:

Application In Synthesis of [ 146137-76-0 ]

  • Downstream synthetic route of [ 146137-76-0 ]

[ 146137-76-0 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 2365-48-2 ]
  • [ 146137-76-0 ]
  • [ 146137-90-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride 1.) DMSO, 20 deg C, 2.) DMSO, 2-5 min; Yield given. Multistep reaction;
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; 7 A mixture of 5.00 g of 2-fluoro-5-iodobenzaldehyde, 2.76 g of methyl thioglycolate, 5.53 g of potassium carbonate,and 50 ml of N,N-dimethylformamide was stirred for 2 hours at 80°C. The reaction mixture was cooled to roomtemperature, and then the precipitated solids were separated by filtration. Concentrated hydrochloric acid was addedto the filtrate, and the precipitated solids were collected by filtration and dried under reduced pressure, thereby obtaining953 mg of 5-iodobenzo[b]thiophene-2-carboxylic acid (hereinafter, described as a "compound 15 of the present invention").
With triethylamine In dimethyl sulfoxide at 20 - 70℃; for 5h; Inert atmosphere; Methyl 7-iodobenzo[b]thiophene-2-carboxylate (11) General procedure: The crude starting material (10) was dissolved in DMSO (25 mL) and methyl thioglycolate (2.6 mL, 1.1 equiv.) was added dropwise under Ar at RT. Triethylamine (7.45 mL, 2.2 equiv.) was then added and the mixture was heated at 70 °C for 5 hours. The reaction mixture was cooled to RT and poured slowly into vigorously stirred ice-water (250 mL). After 30 min of stirring, a light yellow precipitate was collected by filtration, rinsed with H2O, and dried in vacuo to afford a crude yellow solid (6.40 g, 80% crude yield). The product was used for the next reaction without further purification.
  • 2
  • [ 352-34-1 ]
  • [ 33513-42-7 ]
  • [ 146137-76-0 ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide 1.) hexane, THF, -78 deg C, 2.) -78 deg C; Yield given. Multistep reaction;
Stage #1: 4-fluoro-1-iodobenzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; 2-Fluoro-3-iodobenzaldehyde (10) General procedure: To a stirred solution of 1-fluoro-2-iodobenzene (4.6 mL, 39 mmol) in THF (39 mL)at -78°C was added 1.8 M LDA solution (22.8 mL, 1.05 equiv.) dropwise over 10 minunder Ar. After 10 min, DMF (3.65 mL, 1.2 equiv.) was added dropwise and the reactionwas stirred for 10 min at -78°C. The reaction was quenched at -78°C by the rapid additionof 10 mL of acetic acid followed by 80 mL of H2O. The cooling bath was removed, andthe aqueous phase was extracted with diethyl ether (70 mL x 3). The organic layers werecombined and washed with 0.5 N HCl solution (150 mL x 2), H2O (150 mL x 2), and brine(150 mL). The organic solution was dried over MgSO4, filtered, and concentrated underreduced pressure. The resulting brown solid (6.25 g, 64% crude yield) was dried in vacuoand used for the next reaction without further purification.
  • 3
  • [ 146137-76-0 ]
  • [ 334971-55-0 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: 2-Fluoro-5-iodo-benzaldehyde With sodium hydroxide; hydroxylamine hydrochloride In ethanol; water at 25 - 30℃; for 2h; Ice cooling; Stirring; Stage #2: With hydrogenchloride In ethanol; water at 25 - 30℃; 50 PREPARATIONS; Preparation 50; 2-Fluoro-5-iodobenzaldehyde Oxime To a mixture of 2-fluoro-5-iodobenzaldehyde (9.4 mmol) in H2O (5 ml), EtOH (5 ml), and ice (4.5 g) was added hydroxylamine hydrochloride (0.67 g, 10.3 mmol, 1.1 eq.). Then, 23.6 mmol of 50% NaOH (1 g in 1 ml H2O, 2.5 eq.) was added with stirring. Enough ice to keep the temperature at 25-30° C. was added. The reaction was stirred for 2 h, acidified with conc. HCl to pH 4 (ice was added to keep the temperature at 25-30° C.), and extracted with Et2O. The combined organic solution was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel using (1-10%) ethyl acetate in hexanes to give 2-fluoro-5-iodobenzaldehyde oxime (2.06 g, 78% over 2 steps). [00443] MS (ES) (m/z) 264.0 [M-1]. IR (KBr) 3575.39, 1478.30, 1262.00, 1238.75, 1109.23, 964.08, 810.03, 809.87 cm-1.
With hydroxylamine hydrochloride; sodium carbonate In methanol; water at 20℃; for 2h; 1.1.1 General procedure of preparation of 2 General procedure: To a mixture of aldehyde 1 (10.0 mmol) in 30% methanol aqueous solution, NH2OH·HCl (0.695 g, 10.0 mmol) was added slowly. After the NH2OH·HCl was fully dissolved, Na2CO3 (0.53 g 5.0 mmol) was added and then the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The organic phase was dried to afford intermediate 2 as white solids.
  • 4
  • [ 699016-02-9 ]
  • [ 146137-76-0 ]
  • [ 699016-31-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 2h; 117 Preparation 117 Under nitrogen at room temperature, to a solution of 2,2,2-trifluoro-N-[(1R)-2-(4-mercaptophenyl)-1-methylethyl]acetamide (2.0 g) in N,N-dimethylformamide (20 ml) was added 2-fluoro-5-iodobenzaldehyde (2.09 g) and potassium carbonate (1.15 g), and the mixture was stirred at 60° C. for 2 hours.The resulting mixture was poured into water and the aqueous mixture was extracted with ethyl acetate.The organic layer was washed successively with water (two times) and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure.The residue was purified by column chromatography on silica gel (hexane/chloroform=1:3 to only chloroform) to give 2,2,2-trifluoro-N-[(1R)-2-[4-[(2-formyl-4-iodophenyl)thio]phenyl]-1-methylethyl]acetamide (3.06 g). (+)ESI-MS (m/z): 516 (M+Na)+
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 2h; 117 Under nitrogen at room temperature, to a solution of 2,2, 2-TRIFLUORO-N-[(LR)-2-(4-MERCAPTOPHENYL)-1- methylethyl] acetamide (2.0 g) in N, N-dimethylformamide (20 ml) was added 2-FLUORO-5-IODOBENZALDEHYDE (2.09 g) and potassium carbonate (1.15 g), and the mixture was stirred at 60°C for 2 hours. The resulting mixture was poured into water and the aqueous mixture was extracted with ethyl acetate. The organic layer was washed successively with water (two times) and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/chloroform = 1: 3 to only chloroform) to give 2,2, 2- TRIFLUORO-N- [ (1R)-2- [4- [ (2-FORMYL-4-IODOPHENYL) THIO] PHENYL]- 1-METHYLETHYL] ACETAMIDE (3.06 g). (+) ESI-MS (m/z): 516 (M+Na) +
  • 5
  • [ 146137-76-0 ]
  • [ 438050-27-2 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 2-Fluoro-5-iodo-benzaldehyde With sodium tetrahydroborate In methanol at 0 - 20℃; for 1.33333h; Stage #2: With water In ethyl acetate 17.1 Step 1) (2-Fluoro-5-iodo-phenyl)-methanol Step 1) (2-Fluoro-5-iodo-phenyl)-methanol To an ice cooled solution of 2-Fluoro-5-iodo-benzaldehyde (1.0 g, 4.0 mmol) in CH3OH (10 mL) was added NaBH4 (0.182 g, 4.8 mmol) in two portions over 10 min. The reaction mixture was stirred for 1 h and concentrated in vacuo. The residue was dissolved in EtOAc (50 mL) and washed sequentially with 2*H2O (20 mL) and brine (20 mL). The organic layer was dried (MgSO4), and concentrated. The crude material was purified by flash chromatography (30% Ethyl acetate/Petroleum Ether) to afford the titled compound (1.0 g, 99%) as a white solid, identified by NMR and mass spectral analyses. Mp: 42° C. MS (EI+): 252 (M+).
88% With sodium tetrahydroborate In tetrahydrofuran; methanol 33 Dissolve 2-fluoro-5-iodobenzaldehyde, (prepared essentially as described in Tet. Lett., 33, 7499, (1992)), (6. 54 g, 26. 1 mmol) in 4 : 1 tetrahydrofuran : methanol (200 mL) and treat with sodium borohydride (1. 98 g, 52. 3 mmol) and stir overnight. Concentrate the reaction mixture, then partition between ethyl acetate and water. Wash the organic layer with an aqueous saturated solution of sodium chloride, dry (sodium sulfate), filter, and concentrate. Purify the crude oil by silica gel chromatography, eluting with 85 : 15 hexanes : ethyl acetate, to give the title compound as a white crystalline solid (5. 8 g, 88%). 1HNMR (400 MHz, DMSO-d6) 6 4. 46 (d, J = 5. 7 Hz, 2H), 5. 31 (t, J = 5. 7 Hz, 1H), 6. 96 (dd, J = 10. 1, 8. 8 Hz, 1H), 7. 58 (ddd, J = 8. 6, 4. 8, 2. 4 Hz, 1H), 7. 72 (dd, J = 6. 8, 2. 4 Hz, 1H).
  • 6
  • [ 866683-29-6 ]
  • [ 146137-76-0 ]
  • [ 866683-74-1 ]
YieldReaction ConditionsOperation in experiment
45% With tetrabutyl ammonium fluoride; triethylamine In tetrahydrofuran at -78 - 60℃; for 2.16667h; 38 Combine 5-trimethylsilanylethynyl-nicotinonitrile (1. 30 g, 11. 5 mmol), (prepared as described in PREPARATION 3), 2-fluoro-5-iodobenzaldehyde (3. 45 g, 13. 8 mmol, (prepared essentially as described in Tet. Lett., 33, 7499, (1992)), bis (triphenylphosphine) palladium (II) dichloride (404 mg, 0. 575 mmol), copper (I) iodide (219 mg, 1. 15 mmol), and triethylamine (22. 4 mL, 161 mmol) in tetrahydrofuran (9 mL). Cool the suspension to-78 °C and treat with a 1. 0 M solution of tetrabutylammonium fluoride (11. 5 mL) in tetrahydrofuran. After 10 min, heat to 60 °C for 2 h. Cool to room temperature and filter through diatomaceous earth washing with ethyl acetate. Purify the crude product by silica gel chromatography, eluting with a gradient from 80 : 20 to 60 : 40 hexanes : ethyl acetate, to give the title compound as an off-white crystalline solid (1. 3 g, 45%). 1HNMR (400 MHz, DMSO-d6) 6 7. 51 (dd, J = 10. 5, 8. 8 Hz, 2H), 7. 93 (ddd, J = 8. 7, 4. 9, 2. 3 Hz, 1H), 8. 02 (dd, J = 6. 6, 2. 2 Hz, 1H), 8. 56 (t, J = 2. 2 Hz, 1H), 9. 01 (d, J = 2. 2 Hz, 1H), 9. 02 (d, J = 2. 2 Hz, 1H), 10. 16 (s, 1H) ; MS (ES) : 7n/z = 251. 0 [M-H]-.
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