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[ CAS No. 1000801-78-4 ]

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Chemical Structure| 1000801-78-4
Chemical Structure| 1000801-78-4
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Product Details of [ 1000801-78-4 ]

CAS No. :1000801-78-4 MDL No. :MFCD16659011
Formula : C12H19BN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :234.10 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1000801-78-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1000801-78-4 ]

  • Downstream synthetic route of [ 1000801-78-4 ]

[ 1000801-78-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 269410-08-4 ]
  • [ 106-95-6 ]
  • [ 1000801-78-4 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hexamethyldisilazane; In tetrahydrofuran; at 70℃; INTERMEDIATE 36; l-Allyl-4-(4,4.5.5-tetramethyl-ri,3.21dioxaborolan-2-vn-lH'-pyrazole; A mixture of 4-pyrazoleboronic acid pinacol ester (3.0g, 15.6 mmol), allyl bromide (6.9 g, 77 mmol) and sodium Z?(trimethylsilyl)amide (20.5 mL of a 1.5N solution in THF, 30.7 mmol) in THF (20 mL) was heated to 7O0C overnight. After cooling to r.t. the reaction was quenched with water (15 mL) and extracted with EtOAc (2 x 30 mL). The combined organic fractions were washed with brine (50 mL), dried (MgSO4) and concentrated in vacuo to give the title compound (3.4 g, 94%) as a yellow oil. δH (CDCl3) 1.20 (12H, s), 4.61-4.67 (2H, m), 5.06-5.24 (2H, m), 5.79-6.01 (IH, m), 7.60 (IH, s), 7.69 (IH, s).
39% With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 1.0h;Microwave irradiation; 621 mg of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 2.08 g of caesium carbonate, 16 mL, of dimethylformamide and 0.55 mL of allyl bromide are introduced into a microwave reactor of suitable size. The mixture is irradiated for 1 hour at 100 C. The suspension obtained is diluted with ethyl acetate and washed with aqueous sodium bicarbonate solution. The aqueous phase is extracted with ethyl acetate and the organic phases are then combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 292 mg (39%) of 1-(prop-2-enyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 176.LC-MS (7 min): Rt (min)=3.68; [M+H]+: m/z 235.
  • 2
  • 2-(6-bromo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-7,7-dimethyl-5,6,7,8-tetrahydro-4H-[1,3]thiazolo[5,4-c]azepin-4-one [ No CAS ]
  • [ 1000801-78-4 ]
  • 2-[6-(1-allyl-1H-pyrazol-4-yl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-7,7-dimethyl-5,6,7,8-tetrahydro-thiazolo[5,4-c]azepin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With potassium phosphate; tetrabutylammomium bromide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 140℃; for 0.333333h;Microwave irradiation; INTERMEDIATE 47; 2-r6-α-Allyl-lH-pyrazol-4-ylV2,3-dihvdro-benzori,41oxazin-4-yll-7.7-dimethyl-5,6J,8- tetrahydro-thiazolor5,4-clazepin-4-one; Using Example 67 (0.95 g, 2.32 mmol), Intermediate 36 (1.08 g, 4.64 mmol), tetrakis(triphenylphosphine)palladium(0) (549 mg, 0.46 mmol), potassium phosphate (1.47 g, 6.9 mmol) and tetra-n-butylammonium bromide (749 mg, 2.32 mmol) in TηF (10 mL) and water (3 mL) heated to 14O0C under microwave irradiation for 20 minutes. Purification by column chromatography (SiO2, gradient elution 10% EtOAc in DCM increasing to 100% EtOAc) gave the title compound (410 mg, 41%) as a yellow oil. 5η (CDCl3) 1.12 (6η, s), 2.86 (2H, s), 3.13 (2H, d, J 5.3 Hz), 4.08-4.19 (2H, m), 4.27-4.35 (2H, m), 4.73-4.81 (2H, m), 5.23-5.35 (2H, m), 5.83 (IH, br.s), 5.97-6.16 (IH, m), 6.93 (IH, d, J 8.3 Hz), 7.15 (IH, dd, J 8.5, 2.1 Hz), 7.59 (IH, s), 7.73 (IH, s), 8.03 (IH, d, J 2.1 Hz).
  • 3
  • [ 1067172-02-4 ]
  • [ 1000801-78-4 ]
  • 2-[6-(1-allyl-1H-pyrazol-4-yl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With potassium phosphate; tetrabutylammomium bromide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 140℃; for 0.333333h;Microwave irradiation; INTERMEDIATE 48; 2-r6-(l-Allyl-lH-pyrazol-4-yl')-2.3-dihvdro-benzorL41oxazin-4-yll-5.5-dimethyl-5.6- dihydro-4H-benzothiazol-7-one; Using Example 1 (1.1 g, 2.76 mmol), Intermediate 36 (1.29 g, 5.53 mmol), tetrakis(triphenylphosphine)palladium(0) (661 mg, 0.55 mmol), potassium phosphate (1.76 g, 8.3 mmol) and tetra-n-butylammonium bromide (894 mg, 2.76 mmol) in THF (10 mL) and water (5 mL) heated to 14O0C under microwave irradiation for 20 minutes.Purification by column chromatography (SiO2, gradient elution 10% EtOAc in heptane increasing to 100% EtOAc) gave the title compound (400 mg, 34%) as a yellow oil. δϖ(CDCl3) 1.16 (6H, s), 2.43 (2H, s), 2.77 (2H, s), 4.21-4.27 (2H, m), 4.31-4.38 (2H, m), 4.74-4.82 (2H, m), 5.23-5.36 (2H, m), 5.98-6.16 (IH, m), 6.96 (IH, d, J 8.5 Hz), 7.20(IH, dd, J 8.5, 2.1 Hz), 7.60 (IH, s), 7.73 (IH, s), 7.99 (IH, d, J 1.9 Hz).
  • 4
  • [ 1000801-78-4 ]
  • [ 1331786-49-2 ]
  • [ 1201790-48-8 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 130 - 140℃; for 1.5h;Inert atmosphere; Microwave irradiation; 28 mg of the product of step 5 175, 22 mg of boronate 176 prepared in step 6, 30 mg of caesium carbonate, 0.45 mL of dioxane, 5 mg of 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium(II) and 50 μl of water are introduced into a microwave reactor of suitable size, under argon. The mixture is irradiated for 30 minutes at 130 C. A further 4 mg of 1,1'-bis(diphenylphosphino)ferrocene-dichloropalladium(II), 15 mg of boronate 176 prepared in step 6, and 0.1 mL of dioxane are added and this mixture is irradiated for a further 1 hour at 140 C. The suspension obtained is diluted with ethyl acetate and washed with water. The aqueous phase is extracted with ethyl acetate and the organic phases are then combined, dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a 100/0 to 96/4 dichloromethane/methanol mixture to give 8 mg of methyl 4-{6-[1-(prop-2-en-1-yl)-1H-pyrazol-4-yl]-9H-pyrrolo[2,3-b:5,4-c']dipyrid-4-yl}benzoate 177 in the form of an ochre-coloured solid.1H NMR (400 MHz, DMSO-d6) δ ppm: 3.96 (s, 3 H); 4.77 (broad d, J=5.7 Hz, 2 H); 5.15 (broad d, J=16.9 Hz, 1 H); 5.21 (broad d, J=9.8 Hz, 1 H); 5.96 to 6.11 (m, 1 H); 7.28 (d, J=4.9 Hz, 1 H); 7.61 (s, 1 H); 7.67 (s, 1 H); 7.93 (d, J=8.3 Hz, 2 H); 8.00 (s, 1 H); 8.27 (d, J=8.3 Hz, 2 H); 8.65 (d, J=4.9 Hz, 1 H); 8.90 (s, 1 H); 12.34 to 12.41 (broad s, 1 H).LC-MS (7 min): Rt (min)=3.19; [M+H]+: m/z 410; [M-H]-: m/z 408.
  • 5
  • [ 1000801-78-4 ]
  • N-((5-((2-chloropyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)-2-methoxy-2-methylpropanamide [ No CAS ]
  • N-((5-((2-(1-allyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)-2-methoxy-2-methylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
14.6% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere; Example 172 A mixture of Example C5 (0.12 g, 0.33 mmol), <strong>[1000801-78-4]1-allyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (0.085 g, 0.36 mmol) and K2CO3 (0.14 g, 0.99 mmol) in dioxane (4 mL) and H2O (1 mL) was sparged with Ar, treated with Pd(PPh3)4 (0.040 g, 0.034 mmol), sparged again with Ar and heated at 90 C. overnight. The mixture was cooled to RT, treated with satd. NaHCO3, extracted with EtOAc (3*) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via reverse phase silica gel chromatography (MeCN/H2O (0.1% TFA)) to obtain N-((5-((2-(1-allyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)-2-methoxy-2-methylpropanamide (22 mg, 14.6%). 1H NMR (400 MHz, DMSO-d6): δ 10.83 (s, 1H), 10.21 (br s, 1H), 8.41 (d, J=5.8 Hz, 1H), 8.33 (s, 1H), 8.28 (d, J=2.9 Hz, 1H), 8.05 (s, 1H), 8.03 (br s, 1H), 7.76 (dd, J=9.0, 2.9 Hz, 1H), 7.31 (d, J=2.4 Hz, 1H), 6.77 (d, J=5.7 Hz, 1H), 6.02 (m, 1H), 5.21 (m, 1H), 5.13 (m, 1H), 4.77 (d, J=5.8 Hz, 2H), 3.21 (s, 3H), 1.36 (s, 6H); MS (ESI) m/z: 437.2 (M+H+).
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