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[ CAS No. 94278-68-9 ] {[proInfo.proName]}

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Chemical Structure| 94278-68-9
Chemical Structure| 94278-68-9
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Product Details of [ 94278-68-9 ]

CAS No. :94278-68-9 MDL No. :MFCD04115925
Formula : C8H7BrF2O Boiling Point : -
Linear Structure Formula :- InChI Key :JCRQCVDDBZVTMB-UHFFFAOYSA-N
M.W : 237.04 Pubchem ID :3354272
Synonyms :

Calculated chemistry of [ 94278-68-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.69
TPSA : 9.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 2.65
Log Po/w (WLOGP) : 3.56
Log Po/w (MLOGP) : 3.44
Log Po/w (SILICOS-IT) : 3.67
Consensus Log Po/w : 3.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.22
Solubility : 0.144 mg/ml ; 0.000607 mol/l
Class : Soluble
Log S (Ali) : -2.49
Solubility : 0.758 mg/ml ; 0.0032 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.35
Solubility : 0.0107 mg/ml ; 0.000045 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 94278-68-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 94278-68-9 ]

* 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.

  • Downstream synthetic route of [ 94278-68-9 ]

[ 94278-68-9 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 79538-27-5 ]
  • [ 94278-68-9 ]
YieldReaction ConditionsOperation in experiment
66% With phosphorus(V) oxybromide In tetrahydrofuran at 20℃; for 2h; 56.3 Step3: Step3: To a cold stirring solution of (2,6-difluoro-4-methoxyphenyl)MeOH (0.5 g, 2.87 mmol, 1 eq) in THF (20 ml) was portion wise added ROB FontWeight="Bold" FontSize="10" (1.65 g, 5.74 mmol, 2 eq). The reaction mixture then stirred for 2 h at RT. The reaction mixture was quenched by saturated NaHCCb solution under cooling conditions. The organic layer was separated and aqueous layer was extracted by EtOAc (50 ml). The combined organic layer was washed by water (30 ml) and brine (30 ml). [71] The organic layer was dried over anhydrous Na2SC>4, concentrated under reduced pressure to get the crude material which was purified by silica gel (230-400 mesh silica gel; 10% EtO Ac/hexane; R value-0.5) to afford 2-(bromomethyl)-1,3-difluoro-5-methoxybenzene (0.45 g, 66%) as color less liquid.
With hydrogen bromide; acetic acid for 0.75h; Heating;
  • 2
  • [ 79538-28-6 ]
  • [ 94278-68-9 ]
  • 3
  • [ 84937-82-6 ]
  • [ 94278-68-9 ]
  • 4
  • potassium cyanide [ No CAS ]
  • [ 94278-68-9 ]
  • [ 886499-03-2 ]
YieldReaction ConditionsOperation in experiment
48% In water; N,N-dimethyl-formamide at 20℃; for 0.5h; 56.4 Step4: Step4: To a cold stirring solution of 2-(bromomethyl)-l,3-difluoro-5-methoxybenzene (9.5 g, 40.08 mmol, 1 eq) in DMF (38 ml) was slowly added a solution of KCN (3.23 g, 49.7 mmol, 1.24 eq) in water (7.34 ml). The reaction mixture then stirred for 30 min at RT. Water (48 ml) and NaHCCb solution (48 ml) were added to the reaction mixture. The reaction mixture was then extracted by Et20 (2 x 200 ml). The combined organic layer was washed by water (4 x 80 ml) followed by brine (200 ml). The organic layer was dried over anhydrous Na2SC>4, concentrated under reduced pressure to get the crude material, which was purified by silica gel (230-400 mesh silica gel; 10% EtOAc/hexane; Rvalue-0.4) to afford 2-(2,6-difluoro-4-methoxyphenyl)acetonitrile (3.5 g, 48%) as color less liquid.
In water; N,N-dimethyl-formamide Cooling with water bath; 3.A Step A: Preparation of 2,6-Difluoro-4-methoxybenzeneacetonitrileA solution of KCN (0.88 g, 13 mmol) dissolved in water (2 mL) was added dropwise to a water-bath-cooled solution of 2,6-difluoro-4-methoxybenzyl bromide (2.50 g, 10.5 mmol) in Λ/,Λ/-dimethylformamide (10 mL). The reaction mixture was stirred for 20 min. Water was added (20 mL) and then the reaction mixture was poured into saturated aqueous NaΗCC>;3 solution (20 mL) and extracted with ether (50 mL). The organic phase was washed with water (5 x 25 mL), dried over MgSOφ and concentrated to give an oil, which crystallized on standing to provide the title compound as a white solid (1.9 g). 1H NMR δ 6.50 (m, 2H), 3.80 (s, 3H), 3.65 (s, 2H)
In water; N,N-dimethyl-formamide for 0.333333h; 2.A A solution of KCN (0.88 g, 13 mmol) dissolved in water (2 mL) was added dropwise to a water-bath-cooled solution of 2,6-difluoro-4-methoxybenzyl bromide (2.50 g, 10.5 mmol) in N,N-dimethylformamide (10 mL). The reaction mixture was stirred for 20 min. Water was added (20 mL) and then the reaction mixture was poured into saturated aqueous NaHCC^ solution (20 mL) and extracted with ether (50 mL). The organic phase was washed with water (5 x 25 mL), dried over MgSC^, and concentrated to give an oil, which crystallized on standing to provide the title compound as a white solid (1.9 g)..H NMR δ 6.50 (m, 2H), 3.80 (s, 3H), 3.65 (s, 2H).
  • 5
  • [ 94278-68-9 ]
  • [ 1242015-79-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide; water / 0.33 h 2: sodium ethanolate / ethyl acetate; ethanol; xylene / 4 h / 50 °C 3: acetic acid / ethanol / 16 h / Reflux 4: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 20 °C / Cooling with ice 5: potassium carbonate / palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 22 h / Inert atmosphere; Reflux
  • 6
  • [ 94278-68-9 ]
  • [ 1242020-16-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; water / 0.33 h 2: sodium ethanolate / ethyl acetate; ethanol; xylene / 4 h / 50 °C
  • 7
  • [ 94278-68-9 ]
  • [ 1242020-17-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; water / 0.33 h 2: sodium ethanolate / ethyl acetate; ethanol; xylene / 4 h / 50 °C 3: acetic acid / ethanol / 16 h / Reflux
  • 8
  • [ 94278-68-9 ]
  • [ 1242020-18-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide; water / 0.33 h 2: sodium ethanolate / ethyl acetate; ethanol; xylene / 4 h / 50 °C 3: acetic acid / ethanol / 16 h / Reflux 4: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 20 °C / Cooling with ice
  • 9
  • [ 1534390-60-7 ]
  • [ 94278-68-9 ]
  • [ 1534389-48-4 ]
YieldReaction ConditionsOperation in experiment
58 mg With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5h; 4-(2,6-Difluoro-4-methoxybenzyl)-2-(5,6-dimethylpyridin-3-yl)-2H-1 ,2,4- benzothiadiazin-3(4H)-one 1 ,1 -dioxide (178) 4-(2,6-Difluoro-4-methoxybenzyl)-2-(5,6-dimethylpyridin-3-yl)-2H-1 ,2,4- benzothiadiazin-3(4H)-one 1 ,1 -dioxide (178) The title compound (58 mg, 0.13 mmol) was prepared from 2-(5,6-dimethylpyridin-3- yl)-2/-/-1 ,2,4-benzothiadiazin-3(4/-/)-one 1 , 1-dioxide (lntA29) (150 mg, 0.49 mmol), 2,6-difluoro-4-methoxybenzyl bromide (129 mg, 0.54 mmol) and K2C03 (102 mg, 0.74 mmol) in DMF (3 mL) at 50°C using the methods of (115). LCMS (Method B): m/z 460.0 (M+H)+ (ES+), at 4.32 min, 95% 1H NMR: (400 MHz, CDCI3) δ: 2.38 (s, 3H), 2.60 (s, 3H), 3.77 (s, 3H), 5.45 (s, 2H), 6.43-6.51 (m, 2H), 7.35 (t, J=7.5, 1 H), 7.49-7.51 (m, 1 H), 7.62-7.73 (m, 2H), 7.93 (dd, J=7.8, 1.5, 1 H), 8.37 (d, J=2.3, 1 H)
  • 10
  • [ 1534390-00-5 ]
  • [ 94278-68-9 ]
  • [ 1534390-52-7 ]
YieldReaction ConditionsOperation in experiment
301 mg With potassium carbonate In N,N-dimethyl-formamide at 20 - 27℃; for 5h; 1 Step 1 : Preparation of te/f-butyl {6-[4-(2,6-difluoro-4-methoxybenzyl)-1 , 1-dioxido-3- oxo-3,4-dihydro-2/-/-1 ,2,4-benzothiadiazin-2-yl]-3-methoxypyridin-2- yl}methyl carbamate Step 1 : Preparation of te/f-butyl {6-[4-(2,6-difluoro-4-methoxybenzyl)-1 , 1-dioxido-3- oxo-3,4-dihydro-2/-/-1 ,2,4-benzothiadiazin-2-yl]-3-methoxypyridin-2- yl}methyl carbamate The title compound (301 mg, 0.51 mmol) was prepared from te/f-butyl [6-(1 , 1- dioxido-3-oxo-3,4-dihydro-2H-1 ,2,4-benzothiadiazin-2-yl)-3-methoxypyridin-2- yl]methylcarbamate (lntA31) (343 mg, 0.79 mmol), 2,6-difluoro-4-methoxybenzyl bromide (225 mg, 0.95 mmol) and K2C03 (164 mg, 1.19 mmol) in DMF (4 ml_) at rt using the methods of (1 15). LCMS (Method B): m/z 591.2 (M+H)+ (ES+), at 5.04 min, 100%
  • 11
  • [ 1534389-78-0 ]
  • [ 94278-68-9 ]
  • [ 1534389-13-3 ]
YieldReaction ConditionsOperation in experiment
38 mg With potassium carbonate In N,N-dimethyl-formamide at 100℃; Sealed tube;
  • 12
  • [ 1534389-82-6 ]
  • [ 94278-68-9 ]
  • [ 1534389-16-6 ]
YieldReaction ConditionsOperation in experiment
92 mg With potassium carbonate In N,N-dimethyl-formamide at 100℃; Sealed tube;
  • 13
  • [ 1534389-81-5 ]
  • [ 94278-68-9 ]
  • [ 1534389-20-2 ]
YieldReaction ConditionsOperation in experiment
38 mg With potassium carbonate In N,N-dimethyl-formamide at 100℃; Sealed tube;
  • 14
  • [ 941882-18-4 ]
  • [ 94278-68-9 ]
  • [ 1534388-69-6 ]
YieldReaction ConditionsOperation in experiment
59 mg With potassium carbonate In N,N-dimethyl-formamide at 100℃; Sealed tube;
  • 15
  • (S)-methyl-3,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate [ No CAS ]
  • [ 94278-68-9 ]
  • (S)-Methyl 1-(2,6-difluoro-4-methoxybenzyl)-3,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: (S)-methyl-3,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 5℃; for 0.25h; Inert atmosphere; Stage #2: 4-(bromomethyl)-3,5-difluorophenyl methyl ether In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; 149 Preiaration 51: (8)-Methyl 1-(2,6-difluoro-4-methoxybenzyfl-,4-dimethyl-2-oxo-1,2,,4-tetrahydro1uinazoline-7-carboxylate To a stirred solution of (S)-methyl 3,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinazoline-7- carboxylate (Preparation 14) (o.i g, 0.43 mmol) in DMF ( mL) was added NaH (0.014g, 60% suspension in mineral oil) at 0-5 oC under an inert atmosphere and the whole allowed to stir for 15 mm. Then, 2-(bromomethyl)-1,3-difluoro-5-methoxybenzene (0.119 g, 0.47 mmol) was added into the reaction mixture which was allowed to further stir at RT for 2 h. The progress of the reaction was monitored by TLC and LCMS and after completion the mixture was quenched with a saturated solution of NH4C1 andextracted with EtOAc. The organics were washed with cold water followed by brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure to give titled compound (0.166 g, 100% yield and purity >95%) as a white solid. LCMS m/z: 391.14 [M+H].
  • 16
  • [ 94278-68-9 ]
  • (S)-1-(4-(allyloxy)-2,6-difluorobenzyl)-3,4-dimethyl-2-oxo-N-(2,4,6-trifluorobenzyl)-1,2,3,4-tetrahydroquinazoline-7-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
  • 17
  • [ 94278-68-9 ]
  • (4S)-1-(4-(2,3-dihydroxypropoxy)-2,6-difluorobenzyl)-3,4-dimethyl-2-oxo-N-(2,4,6-trifluorobenzyl)-1,2,3,4-tetrahydroquinazoline-7-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone / 0.5 h / 20 °C
  • 18
  • [ 94278-68-9 ]
  • (S)-1-(4-((R)-2,3-dihydroxypropoxy)-2,6-difluorobenzyl)-3,4-dimethyl-2-oxo-N-(2,4,6-trifluorobenzyl)-1,2,3,4-tetrahydroquinazoline-7-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 6.1: AD-mix-α / water; <i>tert</i>-butyl alcohol / 0 - 5 °C
  • 19
  • [ 94278-68-9 ]
  • (S)-1-(4-((S)-2,3-dihydroxypropoxy)-2,6-difluorobenzyl)-3,4-dimethyl-2-oxo-N-(2,4,6-trifluorobenzyl)-1,2,3,4-tetrahydroquinazoline-7-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 6.1: AD-mix-β / water; <i>tert</i>-butyl alcohol / 0 - 5 °C
  • 20
  • [ 94278-68-9 ]
  • (S)-N,1-bis(2,6-difluoro-4-methoxybenzyl)-3,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3.2: 2 h / 20 °C
  • 21
  • [ 94278-68-9 ]
  • (S)-N,1-bis(2,6-difluoro-4-hydroxybenzyl)-3,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3.2: 2 h / 20 °C 4.1: boron tribromide / dichloromethane / 0.5 h / 0 - 20 °C
  • 22
  • [ 94278-68-9 ]
  • (S)-1-(2,6-difluoro-4-methoxybenzyl)-3,4-dimethyl-2-oxo-N-(2,4,6-trifluorobenzyl)-1,2,3,4-tetrahydroquinazoline-7-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C
  • 23
  • [ 94278-68-9 ]
  • (S)-ethyl-2-(4-((3,4-dimethyl-2-oxo-7-((2,4,6-trifluorobenzyl)carbamoyl)-3,4-dihydroquinazolin-1(2H)-yl)methyl)-3,5-difluorophenoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 - 5 °C 5.2: 0.67 h / 0 - 5 °C
  • 24
  • [ 94278-68-9 ]
  • (S)-dibenzyl ((4-((3,4-dimethyl-2-oxo-7-((2,4,6- trifluorobenzyl)carbamoyl)-3,4-dihydroquinazolin-1(2H)-yl)methyl)-3,5-difluorophenoxy)methyl) phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h 5.2: 3 h / 60 °C / Inert atmosphere
  • 25
  • [ 94278-68-9 ]
  • (S)-dibenzyl (4-((3,4-dimethyl-2-oxo-7-((2,4,6- trifluorobenzyl)carbamoyl)-3,4-dihydroquinazolin-1(2H)-yl)methyl)-3,5-difluorophenyl) phosphite [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: 1H-tetrazole / acetonitrile / 3 h / 20 °C
  • 26
  • [ 94278-68-9 ]
  • (S)-dibenzyl (4-((3,4-dimethyl-2-oxo-7-((2,4,6-trifluorobenzyl)carbamoyl)-3,4-dihydroquinazolin-1(2H)-yl)methyl)-3,5-difluorophenyl) phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: 1H-tetrazole / acetonitrile / 3 h / 20 °C 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere
  • 27
  • [ 94278-68-9 ]
  • (S)-1-(2,6-difluoro-4-methoxybenzyl)-3,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C
  • 28
  • [ 94278-68-9 ]
  • (S)-1-(2,6-difluoro-4-hydroxybenzyl)-3,4-dimethyl-2-oxo-N-(2,4,6-trifluorobenzyl)-1,2,3,4-tetrahydroquinazoline-7-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C
  • 29
  • [ 94278-68-9 ]
  • (S)-1-(2,6-difluoro-4-(2-hydroxyethoxy)benzyl)-3,4-dimethyl-2-oxo-N-(2,4,6-trifluorobenzyl)-1,2,3,4-tetrahydroquinazoline-7-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 - 5 °C 5.2: 0.67 h / 0 - 5 °C 6.1: sodium tetrahydroborate / ethanol / 3 h / 0 - 20 °C
  • 30
  • [ 94278-68-9 ]
  • (S)-1-(2,6-difluoro-4-(3-hydroxypropoxy)benzyl)-3,4-dimethyl-2-oxo-N-(2,4,6-trifluorobenzyl)-1,2,3,4-tetrahydroquinazoline-7-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C
  • 31
  • [ 94278-68-9 ]
  • (S)-3-(4-((3,4-dimethyl-2-oxo-7-((2,4,6-trifluorobenzyl)carbamoyl)-3,4-dihydroquinazolin-1(2H)-yl)methyl)-3,5-difluorophenoxy)propyl dihydrogen phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 6.1: trichlorophosphate / 1 h / 20 °C 6.2: 19 h / 0 - 5 °C
  • 32
  • [ 94278-68-9 ]
  • (S)-(4-((3,4-dimethyl-2-oxo-7-((2,4,6-trifluorobenzyl)carbamoyl)-3,4-dihydroquinazolin-1(2H)-yl)methyl)-3,5-difluorophenoxy)methyl dihydrogen phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h 5.2: 3 h / 60 °C / Inert atmosphere 6.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran
  • 33
  • [ 94278-68-9 ]
  • (S)-4-((3,4-dimethyl-2-oxo-7-((2,4,6-trifluorobenzyl)carbamoyl)-3,4-dihydroquinazolin-1(2H)-yl)methyl)-3,5-difluorophenyl dihydrogen phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: 1H-tetrazole / acetonitrile / 3 h / 20 °C 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 7.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran
  • 34
  • [ 94278-68-9 ]
  • (S)-4-acetamidobenzyl-(4-((3,4-dimethyl-2-oxo-7-((2,4,6-trifluorobenzyl)carbamoyl)-3,4-dihydroquinazolin-1(2H)-yl)methyl)-3,5-difluorophenyl) carbonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C 5.2: 0.5 h / 20 °C
  • 35
  • [ 94278-68-9 ]
  • (S)-benzyl-3-(((4-((3,4-dimethyl-2-oxo-7-((2,4,6-trifluorobenzyl)carbamoyl)-3,4-dihydroquinazolin-1(2H)-yl)methyl)-3,5-difluorophenoxy)carbonyl)(methyl)amino)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C 5.2: 20 h / 80 °C
  • 36
  • [ 94278-68-9 ]
  • [ 122-52-1 ]
  • 2-(diethoxyphosphorylmethyl)-1,3-difluoro-5-methoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.40 g at 140℃; for 6h; Sealed tube; 45.1-a Step 1-a: Preparation of 2-(diethoxyphosphorylmethyl -l ,3-difluoro-5-methoxybenzene: In a re-sealable tube was charged triethyl phosphite (3.54 mL; 20.46 mmol) and 2-(bromomethyl)-l ,3- difluoro-5-methoxybenzene (5.00 g; 20.46 mmol). The tube was sealed and the mixture was heated to 140 °C and stirred for 6 h. After cooling to rt, the mixture was purified by column chromatography (silica gel; PE : EA; 2: 1 ; v/v) to afford 2-(diethoxyphosphorylmethyl)-l ,3-difluoro-5-methoxy-benzene (5.40 g) as a colorless oil. (1016) MS m/z (+ESI): 295.1 [M+H]+.
  • 37
  • [ 94278-68-9 ]
  • tert-butyl 4-[(2,6-difluoro-4-methoxyphenyl)methylene]azepane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 6 h / 140 °C / Sealed tube 2.1: sodium hydride / tetrahydrofuran / 0.5 h 2.2: 16 h
  • 38
  • [ 94278-68-9 ]
  • tert-butyl 4-[(2,6-difluoro-4-methoxyphenyl)methyl]azepane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 6 h / 140 °C / Sealed tube 2.1: sodium hydride / tetrahydrofuran / 0.5 h 2.2: 16 h 3.1: palladium 10% on activated carbon; hydrogen / methanol / 16 h / 750.08 Torr
  • 39
  • 3-[2,6-dimethoxy-5-(methylsulfonyl)pyridin-3-yl]-6-fluoro-1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one [ No CAS ]
  • [ 94278-68-9 ]
  • 1-(2,6-difluoro-4-methoxybenzyl)3-[2,6-dimethoxy-5-(methylsulfonyl)pyridin-3-yl]-6- fluoro-1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
51 mg Stage #1: 3-[2,6-dimethoxy-5-(methylsulfonyl)pyridin-3-yl]-6-fluoro-1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one With sodium hexamethyldisilazane In tetrahydrofuran at 20 - 27℃; for 0.25h; Stage #2: 4-(bromomethyl)-3,5-difluorophenyl methyl ether In tetrahydrofuran at 20 - 27℃; for 3h; 25 Example 25, 1-(2,6-difluoro-4-methoxybenzyl)-3- j2,6-dimethoxy-5-(methylsulfonyl)pyridin-3-ylJ -6-fluoro- 1,3,4 ,5 -tetrahydro-2H- 1 ,3-benzodiazepin-2-one NaHMDS (1M in THF, 0.15 mL, 0.15 mmol) was added to a solution of 3-[2,6- dimethoxy-5-(methylsulfonyl)pyridin-3-yl]-6-fluoro-l,3,4,5-tetrahydro-2H-l,3- benzodiazepin-2-one Intermediate 16, 50 mg, 0.13 mmol) in THF (1 mL) at rt and the mixture stirred at rt for 15 min. A solution of 4-(bromomethyl)-3,5-difluorophenyl methyl ether (Intermediate 22, 36 mg, 0.15 mmol) in THF (0.5 mL) was then added and the reaction mixture was stirred at rt for 3 h before the addition of H20 and EtOAc. The phases were separated, the aqueous phase was extracted with EtOAc, and the combined organic phases were washed with H20 and brine and concentrated in vacuo. Purification by gradient column chromatography, eluting with 0-100% EtOAc in petroleum ether yielded the title compound (51 mg, 0.09 mmol).
  • 40
  • [ 256417-10-4 ]
  • [ 94278-68-9 ]
  • 41
  • [ 94278-68-9 ]
  • ethyl 2-cyano-2-(2,6-difluoro-4-methoxyphenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water; N,N-dimethyl-formamide / 0.5 h / 20 °C 2: sodium ethanolate / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 50 °C
  • 42
  • [ 94278-68-9 ]
  • ethyl 3-amino-2-(2,6-difluoro-4-methoxyphenyl)propanoate hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: water; N,N-dimethyl-formamide / 0.5 h / 20 °C 2: sodium ethanolate / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 50 °C 3: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 2068.65 Torr / Inert atmosphere
  • 43
  • [ 94278-68-9 ]
  • ethyl 2-(2,6-difluoro-4-methoxyphenyl)-3-(3-ethoxy-3-oxopropanamido)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: water; N,N-dimethyl-formamide / 0.5 h / 20 °C 2.1: sodium ethanolate / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 50 °C 3.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 2068.65 Torr / Inert atmosphere 4.1: triethylamine / dichloromethane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C
  • 44
  • [ 94278-68-9 ]
  • ethyl 5-(2,6-difluoro-4-methoxyphenyl)-2,4-dioxopiperidine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: water; N,N-dimethyl-formamide / 0.5 h / 20 °C 2.1: sodium ethanolate / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 50 °C 3.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 2068.65 Torr / Inert atmosphere 4.1: triethylamine / dichloromethane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C 5.1: sodium / toluene; ethanol / 3 h / 0 °C / Reflux
  • 45
  • [ 94278-68-9 ]
  • 5-(2,6-difluoro-4-methoxyphenyl)piperidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: water; N,N-dimethyl-formamide / 0.5 h / 20 °C 2.1: sodium ethanolate / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 50 °C 3.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 2068.65 Torr / Inert atmosphere 4.1: triethylamine / dichloromethane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C 5.1: sodium / toluene; ethanol / 3 h / 0 °C / Reflux 6.1: water; acetonitrile / 3 h / Reflux
  • 46
  • [ 94278-68-9 ]
  • 5-(2,6-difluoro-4-methoxyphenyl)-4-(hydroxyimino)piperidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: water; N,N-dimethyl-formamide / 0.5 h / 20 °C 2.1: sodium ethanolate / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 50 °C 3.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 2068.65 Torr / Inert atmosphere 4.1: triethylamine / dichloromethane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C 5.1: sodium / toluene; ethanol / 3 h / 0 °C / Reflux 6.1: water; acetonitrile / 3 h / Reflux 7.1: hydroxylamine hydrochloride; sodium acetate / ethanol / 16 h / 20 °C
  • 47
  • [ 94278-68-9 ]
  • tert-butyl (5-(2,6-difluoro-4-methoxyphenyl)-2-oxopiperidin-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: water; N,N-dimethyl-formamide / 0.5 h / 20 °C 2.1: sodium ethanolate / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 50 °C 3.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 2068.65 Torr / Inert atmosphere 4.1: triethylamine / dichloromethane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C 5.1: sodium / toluene; ethanol / 3 h / 0 °C / Reflux 6.1: water; acetonitrile / 3 h / Reflux 7.1: hydroxylamine hydrochloride; sodium acetate / ethanol / 16 h / 20 °C 8.1: NiCl4*6H2O / methanol / 0.5 h / -40 °C 8.2: 2 h / -40 - 20 °C 8.3: 16 h / 20 °C
  • 48
  • [ 94278-68-9 ]
  • tert-butyl (5-(2,6-difluoro-4-methoxyphenyl)-1-(2-methoxyethyl)-2-oxopiperidin-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: water; N,N-dimethyl-formamide / 0.5 h / 20 °C 2.1: sodium ethanolate / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 50 °C 3.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 2068.65 Torr / Inert atmosphere 4.1: triethylamine / dichloromethane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C 5.1: sodium / toluene; ethanol / 3 h / 0 °C / Reflux 6.1: water; acetonitrile / 3 h / Reflux 7.1: hydroxylamine hydrochloride; sodium acetate / ethanol / 16 h / 20 °C 8.1: NiCl4*6H2O / methanol / 0.5 h / -40 °C 8.2: 2 h / -40 - 20 °C 8.3: 16 h / 20 °C 9.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 9.2: 16 h / 20 °C
  • 49
  • [ 94278-68-9 ]
  • 1-(4-bromophenyl)-3-(5-(2,6-difluoro-4-methoxyphenyl)-1-(2-methoxyethyl)-2-oxopiperidin-4-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: water; N,N-dimethyl-formamide / 0.5 h / 20 °C 2.1: sodium ethanolate / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / 50 °C 3.1: hydrogenchloride; hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 2068.65 Torr / Inert atmosphere 4.1: triethylamine / dichloromethane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C 5.1: sodium / toluene; ethanol / 3 h / 0 °C / Reflux 6.1: water; acetonitrile / 3 h / Reflux 7.1: hydroxylamine hydrochloride; sodium acetate / ethanol / 16 h / 20 °C 8.1: NiCl4*6H2O / methanol / 0.5 h / -40 °C 8.2: 2 h / -40 - 20 °C 8.3: 16 h / 20 °C 9.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 9.2: 16 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 10.2: 0 - 20 °C
  • 50
  • 1-bromo-2,6-difluoro4-methoxybenzene [ No CAS ]
  • [ 94278-68-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C / Inert atmosphere 1.2: 16 h / -78 - 20 °C / Inert atmosphere 2.1: sodium tetrahydroborate / methanol / 1 h / 20 °C 3.1: phosphorus(V) oxybromide / tetrahydrofuran / 2 h / 20 °C
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