941-91-3|3-Bromo-1-methylquinolin-2(1H)-one| Ambeed

* 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 [ 941-91-3 ]

[ 941-91-3 ] Synthesis Path-Downstream 1~54

1
[ 110-00-9 ]
[ 941-91-3 ]
[ 138073-20-8 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1481 - 1484.

2
[ 188290-36-0 ]
[ 941-91-3 ]
[ 138037-47-5 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1481 - 1484.

3
[ 109-97-7 ]
[ 941-91-3 ]
[ 138037-46-4 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1481 - 1484.

4
[ 941-91-3 ]
[ 85-01-8 ]
[ 138037-43-1 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1481 - 1484.

5
[ 941-91-3 ]
[ 138037-45-3 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1481 - 1484.

6
1,2-dihydro-2-tert-butoxy-3-bromo-1-methylquinoline [ No CAS ]
[ 941-91-3 ]

References: [1]Synthetic Communications,1995,vol. 25,p. 2999 - 3006.

7
[ 941-91-3 ]
[ 146140-95-6 ]
[ 197524-35-9 ]

References: [1]Synlett,1997,vol. 1997,p. 1067 - 1068.

8
[ 939-16-2 ]
[ 74-88-4 ]
[ 941-91-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 16.0h;	To a mixture of 3-bromoquinolin-2(1H)-one (224 mg, 1.0 mmol) in DMF (4 mL) was added CH3I (210 mg, 1.5 mmol), K2CO3 (273 mg, 2.0 mmol) at r.t.. The reaction was stirred at 60 oC for 16 h. The mixture was concentrated in vacuum. The residue was purified by column chromatography on silica gel (PE : EA =5:1 to 1:1) to 3-bromo-1-methylquinolin-2(1H)-one (132 mg, yield 82%) as a white solid.1H NMR (400 MHz, DMSO-d6) delta 8.54 (s, 1H), 7.75 (dd, J = 7.8, 1.2 Hz, 1H), 7.70-7.66 (m, 1H), 7.57 (d, J = 8.5 Hz, 1H), 7.36- 7.24 (m, 1H), 3.71 (s, 3H).

References: [1]Tetrahedron,2008,vol. 64,p. 6030 - 6037.
[2]Patent: WO2019/140387,2019,A1 .Location in patent: Paragraph 00557; 00562; 00563.
[3]Synlett,1997,vol. 1997,p. 1067 - 1068.

11
3-bromo-quinoline iodomethylate [ No CAS ]
[ 941-91-3 ]

References: [1]Chemische Berichte,1882,vol. 15,p. 186.

12
[ 74-88-4 ]
3-bromo-carbostyril sodium [ No CAS ]
[ 941-91-3 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1892,vol. <2> 45,p. 179.
Chemische Berichte,1903,vol. 36,p. 1206.

13
[ 941-91-3 ]
[ 106473-33-0 ]
C₂₄H₂₀N₂SO₅ [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

14
[ 941-91-3 ]
[ 70-55-3 ]
C₁₇H₁₆N₂O₃S [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

15
[ 941-91-3 ]
[ 3144-09-0 ]
C₁₁H₁₂N₂O₃S [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

16
[ 941-91-3 ]
[ 57-13-6 ]
C₃₃H₂₆N₄O₃ [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

17
[ 941-91-3 ]
[ 954416-51-4 ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

18
[ 941-91-3 ]
[ 1201-74-7 ]
C₂₂H₂₀N₂O [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.
[2]ChemMedChem,2011,vol. 6,p. 804 - 815.

19
[ 941-91-3 ]
[ 765-30-0 ]
C₁₃H₁₄N₂O [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

20
[ 941-91-3 ]
[ 3424-93-9 ]
4-methoxy-N-(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 10.0h;Inert atmosphere; Sealed tube;	General procedure: A flame-dried resealable Schlenk tube was charged with Pd(OAc)2 (7.5 mg, 0.05 mmol, 5 mol%), Xantphos (29 mg, 0.05 mmol, 5 mol%), the solid reactant(s) (1.0 mmol of the bromoquinolin-2(1H)-one 6, 1.5 mmol of appropriate amine or amide) and Cs2CO3 (651 mg, 2 mmol). The Schlenk tube was capped with a rubber septum, evacuated and backfilled with argon; this evacuation/backfill sequence was repeated one additional time. The liquid reactant(s) and 1,4-dioxane (2 mL) were added through the septum. The septum was replaced with a teflon screwcap. The Schlenk tube was sealed, and the mixture was stirred at 100 C for 10 h. The resulting suspension was cooled to room temperature and filtred through celite eluting with ethyl acetate, and the inorganic salts were removed. The filtrate was concentrated and purification of the residue through a silica gel column chromatography gave the expected product 7.

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 4995 - 5005.
[2]Tetrahedron,2007,vol. 63,p. 10202 - 10210.
[3]ChemMedChem,2011,vol. 6,p. 804 - 815.
[4]European Journal of Medicinal Chemistry,2012,vol. 52,p. 44 - 50.

21
[ 60-35-5 ]
[ 941-91-3 ]
C₁₂H₁₂N₂O₂ [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.
[2]ChemMedChem,2011,vol. 6,p. 804 - 815.

22
[ 616-45-5 ]
[ 941-91-3 ]
C₁₄H₁₄N₂O₂ [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

23
[ 941-91-3 ]
[ 598-81-2 ]
C₁₃H₁₄N₂O₃ [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.
[2]ChemMedChem,2011,vol. 6,p. 804 - 815.

24
[ 941-91-3 ]
[ 62-53-3 ]
C₁₆H₁₄N₂O [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

25
[ 941-91-3 ]
[ 100-46-9 ]
3-(benzylamino)-1-methylquinolin-2(1H)-one [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.
[2]ChemMedChem,2011,vol. 6,p. 804 - 815.

26
[ 941-91-3 ]
[ 109-73-9 ]
C₁₄H₁₈N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 10.0h;Inert atmosphere; Sealed tube;	General procedure: A flame-dried resealable Schlenk tube was charged with Pd(OAc)2 (7.5 mg, 0.05 mmol, 5 mol%), Xantphos (29 mg, 0.05 mmol, 5 mol%), the solid reactant(s) (1.0 mmol of the bromoquinolin-2(1H)-one 6, 1.5 mmol of appropriate amine or amide) and Cs2CO3 (651 mg, 2 mmol). The Schlenk tube was capped with a rubber septum, evacuated and backfilled with argon; this evacuation/backfill sequence was repeated one additional time. The liquid reactant(s) and 1,4-dioxane (2 mL) were added through the septum. The septum was replaced with a teflon screwcap. The Schlenk tube was sealed, and the mixture was stirred at 100 C for 10 h. The resulting suspension was cooled to room temperature and filtred through celite eluting with ethyl acetate, and the inorganic salts were removed. The filtrate was concentrated and purification of the residue through a silica gel column chromatography gave the expected product 7.

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.
[2]ChemMedChem,2011,vol. 6,p. 804 - 815.
[3]European Journal of Medicinal Chemistry,2012,vol. 52,p. 44 - 50.

27
[ 941-91-3 ]
N-(6-bromo-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-4-methoxybenzamide [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

28
[ 941-91-3 ]
C₂₆H₂₃N₃O₅ [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

29
[ 941-91-3 ]
C₁₄H₁₅BrN₂O₂ [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

30
[ 941-91-3 ]
C₁₈H₂₃N₃O₃ [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 10202 - 10210.

31
[ 22615-00-5 ]
[ 941-91-3 ]

References: [1]Synlett,1997,vol. 1997,p. 1067 - 1068.
[2]Patent: WO2019/140387,2019,A1 .

32
[ 941-91-3 ]
[ 114414-78-7 ]

References: [1]Synlett,1997,vol. 1997,p. 1067 - 1068.

33
[ 941-91-3 ]
[ 197524-37-1 ]

References: [1]Synlett,1997,vol. 1997,p. 1067 - 1068.

34
[ 21979-55-5 ]
[ 941-91-3 ]

References: [1]Synthetic Communications,1995,vol. 25,p. 2999 - 3006.

35
[ 941-91-3 ]
[ 615-36-1 ]
[ 1041015-14-8 ]

References: [1]Tetrahedron,2008,vol. 64,p. 6030 - 6037.

36
[ 941-91-3 ]
3-amino-1-methylquinolin-2(1H)-one [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1677 - 1687.
[2]Patent: WO2019/140387,2019,A1 .

37
[ 101870-60-4 ]
[ 941-91-3 ]

References: [1]Tetrahedron,2011,vol. 67,p. 655 - 659.

38
N-[3-bromo-1-methylquinolin-2(1H)-ylidene]aniline [ No CAS ]
[ 941-91-3 ]

References: [1]Tetrahedron,2011,vol. 67,p. 655 - 659.

39
[ 1263300-33-9 ]
[ 941-91-3 ]

References: [1]Tetrahedron,2011,vol. 67,p. 655 - 659.

40
[ 120-72-9 ]
[ 941-91-3 ]
[ 1309362-69-3 ]

References: [1]European Journal of Organic Chemistry,2011,p. 5077 - 5088.
[2]Journal of Organic Chemistry,2011,vol. 76,p. 4995 - 5005.

41
[ 1006-94-6 ]
[ 941-91-3 ]
[ 1335032-97-7 ]

References: [1]European Journal of Organic Chemistry,2011,p. 5077 - 5088.

42
[ 941-91-3 ]
[ 1561823-24-2 ]

References: [1]Patent: WO2014/23754,2014,A1 .

43
[ 941-91-3 ]
[ 1561823-29-7 ]

References: [1]Patent: WO2014/23754,2014,A1 .

44
[ 941-91-3 ]
[ 1561823-34-4 ]

References: [1]Patent: WO2014/23754,2014,A1 .

45
[ 941-91-3 ]
[ 1561823-36-6 ]

References: [1]Patent: WO2014/23754,2014,A1 .

46
[ 941-91-3 ]
[ 1561823-39-9 ]

References: [1]Patent: WO2014/23754,2014,A1 .

47
[ 941-91-3 ]
[ 1561823-41-3 ]

References: [1]Patent: WO2014/23754,2014,A1 .

48
[ 941-91-3 ]
(S)-1-methyl-N-(7-oxo-1-(5-(2-oxo-1,2-dihydroquinolin-3-yl)oxazol-2-yl)nonyl)azetidine-3-carboxamide monotrifluoroacetate [ No CAS ]

References: [1]Patent: WO2014/23754,2014,A1 .

49
[ 941-91-3 ]
[ 1561823-71-9 ]

References: [1]Patent: WO2014/23754,2014,A1 .

50
[ 941-91-3 ]
[ 121505-93-9 ]
[ 1561823-19-5 ]

Yield	Reaction Conditions	Operation in experiment
	With isopropylmagnesium chloride; In tetrahydrofuran; at 20℃; for 0.5h;	To a 0.3 M solution of 3-bromo-l-methylquinolin-2(lH)-one (1 equiv; prepared as described in Tetrahedron, 64 (26), 6030-6037; 2008) and tert-butyl (2-(methoxy(methyl)amino)-2- oxoethyl)carbamate (1.2 eq) in dry THF, isopropylmagnesium chloride (3 eq) was added dropwise at room temperature. The mixture was stirred for 30 min at room temperature, diluted with dichloromethane, washed with sat. aq. NH4C1 dried (Na2S04) and concentrated under reduced pressure. The residue was purified by flash chromatography (Si02, Pethroleum ether/EtOAc, from 7% to 60% EtOAc). The pooled fractions were concentraded under vacuum to the title compound. MS (ES) C17H20N2O4 requires: 316.35, found: 317. 1H-NMR (400 MHz, DMSO-dg) delta: 8.53 (1 H, s), 7.99 (1 H, d, J = 7.2 Hz), 7.78 (1 H, t, J = 6.8 Hz), 7.61 (1 H, d, J = 8.4 Hz), 7.35 (1 H, t, J = 7.2 Hz), 6.97 (1 H, bt, J = 5.6 Hz), 4.45 (1 H, d, J = 5.6 Hz), 3.70 (3 H, s), 1.39 (9 H, s).

References: [1]Patent: WO2014/23754,2014,A1 .Location in patent: Page/Page column 37-38.

51
[ 939-16-2 ]
[ 74-88-4 ]
[ 941-91-3 ]

Yield	Reaction Conditions	Operation in experiment
52 mg	With potassium carbonate; In water; N,N-dimethyl-formamide; at 20℃; for 16.0h;	Step 1: 3-Bromo-1-methylquinolin-2(1H)-one To a solution of 3-bromo-2-hydroxyquinoline (50 mg, 0.223 mmol) in DMF (1 mL) was added methyl iodide (0.017 mL, 0.268 mmol) and potassium carbonate (46.3 mg, 0.335 mmol.) at room temperature. The reaction mixture was stirred for 16 hours at room temperature. Water was added and the solution was extracted with ethyl acetate. The organic layer was washed with water then aqueous saturated sodium chloride solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=/1) to give 3-bromo-1-methylquinolin-2(1H)-one (52 mg, MS: 238.1 [M+H+].)

References: [1]Patent: US2014/206661,2014,A1 .Location in patent: Paragraph 0427.

52
[ 941-91-3 ]
[ 4981-92-4 ]
3-(1-benzyl-1H-benzo[d]imidazol-2-yl)-1-methylquinolin-2(1H)-one [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 8533 - 8541.

53
[ 941-91-3 ]
[ 341941-85-3 ]
3-(1-(4-methoxybenzyl)-5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-1-methylquinolin-2(1H)-one [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 8533 - 8541.

54
[ 51-17-2 ]
[ 941-91-3 ]
3-(1H-benzo[d]imidazol-2-yl)-1-methylquinolin-2(1H)-one [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 8533 - 8541.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 941-91-3

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CAS No.: 941-91-3

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[ 941-91-3 ] Synthesis Path-Downstream 1~54

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