35979-69-2|4-Bromo-2-methyl-2-butanol| Ambeed

CAS No. :	35979-69-2
Formula :	C₅H₁₁BrO
M.W :	167.04
SMILES Code :	CC(O)(C)CCBr
MDL No. :	MFCD20483824
InChI Key :	RBFVGQWGOARJRU-UHFFFAOYSA-N
Pubchem ID :	10607172

Safety of [ 35979-69-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 35979-69-2 ]

* 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 [ 35979-69-2 ]

[ 35979-69-2 ] Synthesis Path-Downstream 1~54

1
[ 917-64-6 ]
[ 539-74-2 ]
[ 35979-69-2 ]

References: [1]Helvetica Chimica Acta,1979,vol. 62,p. 1854 - 1865.
[2]Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases,1984,vol. 80,p. 3391 - 3398.
[3]Tetrahedron Letters,2000,vol. 41,p. 7337 - 7340.

2
[ 539-74-2 ]
[ 75-16-1 ]
[ 35979-69-2 ]

Yield	Reaction Conditions	Operation in experiment
75.1%	In tetrahydrofuran; at 0℃;	Intermediate 45 4-bromo-2-methylbutan-2-ol To a solution of methyl 3-bromopropanoate (0.2 g, 1.2 mmol,) in THF (5 mL) was added methyl magnesium bromide (2.4 mL, 2.4 mmol) at 0 C. The mixture was stirred at this temperature until the substrate was consumed based on tic [petroleum ether/ethyl acetate (3: 1); product Rf 0.3]. The reaction was quenched with ammonium chloride (2 mL) at 0 C. The mixture was partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated, to give a crude product which was purified by a column chromatography eluting with petroleum ether/ ethyl acetate (3: 1 ) to give 4-bromo-2- methylbutan-2-ol (0.15 g, 75.1 % yield) as a yellow oil.
	In diethyl ether; at 0℃;	a) 4-Bromo-2-methylbutan-2-olTo a cooled solution of ethyl 3-bromopropanoate (0.5 g, 2.8 mmol) in diethyl ether (50 ml) at 0 C was added methyl magnesium bromide (0.98 g, 8.3 mmol, 3 eq.) dropwise over 5 min and the mixture was allowed to stir until TLC showed complete absence of the starting material. The mixture was quenched and extracted as in Inter- mediate Example 5(c). The solvent was distilled off to give the crude product (0.4 g).
	In diethyl ether; at 0℃; for 0.0833333h;	To a cooled solution of ethyl 3-bromopropanoate (0.5 g, 2.8 mmol) in diethyl ether (50 ml) at 0 C. was added methyl magnesium bromide (0.98 g, 8.3 mmol, 3 eq.) dropwise over 5 min and the mixture was allowed to stir until TLC showed complete absence of the starting material. The mixture was quenched and extracted as in Intermediate Example 5(c). The solvent was distilled off to give the crude product (0.4 g).

In diethyl ether; at -20 - 20℃; for 2h;

Methyl magnesium bromide (11.04 mL, 33.14 mmol) was added drop wise over 10 min to a well-stirred mixture of ethyl 3-bromopropanoate (compound 24; 2.0 g, 11.04 mmol) in diethyl ether (25 mL) at -20 C. The reaction mixture was stirred at rt for over 2 h. On completion the reaction mixture was poured into aq. NH4Cl (25 mL) and extracted with EtOAc (2*25 mL). The combined organic layers were washed with H2O (100 mL) and brine (100 mL), separated and then dried over anhydrous Na2SO4. Evaporated under reduced pressure yielded 2.1 g of crude compound 25 which was used directly in the next step without any further purification.

References: [1]Patent: WO2014/143799,2014,A2 .Location in patent: Page/Page column 403.
[2]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 525 - 535.
[3]Journal of Medicinal Chemistry,2022,vol. 65,p. 4767 - 4782.
[4]Journal of Medicinal Chemistry,2021,vol. 64,p. 629 - 643.
[5]Journal of Organometallic Chemistry,1973,vol. 47,p. 337 - 350.
[6]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.
[7]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 828 - 833.
[8]Patent: WO2013/53983,2013,A1 .Location in patent: Page/Page column 32.
[9]Patent: US2015/11548,2015,A1 .Location in patent: Paragraph 0138.
[10]Patent: US2019/263792,2019,A1 .Location in patent: Paragraph 0444; 0445.

3
[ 35979-69-2 ]
[ 603-35-0 ]
[ 67883-18-5 ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 7337 - 7340.
[2]Journal of general chemistry of the USSR,1978,vol. 48,p. 818 - 822.
Zhurnal Obshchei Khimii,1978,vol. 48,p. 897 - 902.

4
[ 107-82-4 ]
[ 35979-69-2 ]

References: [1]Synthesis,1976,p. 523 - 524.

5
[ 3395-91-3 ]
[ 75-16-1 ]
[ 35979-69-2 ]

Yield	Reaction Conditions	Operation in experiment
71.7%	In diethyl ether; at -20℃; for 1h;Inert atmosphere;	In a 250 mL round bottom flask, methyl 3-bromopropanoate (5.0 mL, 45.8 mmol, 1.0 eq.) was taken up in dry ether (55.2 mL, 0.83 M) under nitrogen and cooled to -20 C. To this, 3.0 M methylmagnesium bromide (45.8 ml, 137 mmol, 3.0 eq) was added in dropwise fashion and the resulting mixture was stirred for an hour. The reaction was quenched with aqueous ammonium chloride. The resulting white suspension was extracted with ether multiple times. The combined organics were washed with brine, dried over MgSO4, and concentrated to yield 4-bromo-2-methylbutan-2-ol as an oil (5.49 g, 71.7%)
65%	In diethyl ether; at 0 - 20℃; for 2h;	To a stirred solution of 4-bromo-butyric acid methyl ester (2 g, 12.27 mmol) in diethyl ether (20 mL) is added methyl magnesium bromide (16.4 mL, 49.08 mmol) at 0 C. and the mixture is stirred at room temperature for 2 hours. The reaction mixture is quenched with 1 N HCl and extracted with diethyl ether (2*20 mL). The combined organic extracts are washed with saturated brine solution (20 mL), dried over sodium sulphate, filtered, and concentrated. The crude material is purified with silica gel column chromatography (combiflash) eluting in 20% EtOAc/hexanes to give the title compound (1.3 g, 65%). 1H NMR (400 MHz, CDCl3): δ 3.48 (t, J=8.0 Hz, 2H), 2.16 (t, J=7.4 Hz, 2H), 1.89 (s, 6H), 1.76 (s, 3H), 1.27 (s, 6H).
60%	In diethyl ether; at 0 - 20℃; for 1h;	To a stirred solution of 4-bromo-butyric acid methyl ester (1 g, 5.9 mmol) in diethyl ether (20 mL) is added methyl magnesium bromide (19.9 mL, 23.9 mmol) at 0 C and the mixture is stirred at room temperature for 1 hour. The reaction mixture is quenched with aqueous ammonium chloride (40 mL) and extracted with diethyl ether (2x20 mL). The combined organic extracts are washed with saturated brine solution (20 mL), dried over sodium sulphate, filtered, and concentrated. The crude material is purified by silica gel column chromatography (combiflash) eluting with 20%EtOAc/hexanes to obtain title compound as pale pink liquid (0.6 g, 60%). ^NMR (400 MHz, DMSO) δ 4.38 (s, 1H), 3.52-3.48 (m, 2H), 1.97-1.91 (m, 2H), 1.08 (s, 6H).

48.9%	In tetrahydrofuran; at 0 - 20℃; for 16h;	a) 4-Bromo-2-methylbutan-2-olTo a solution of methyl 3-bromopropanoate (5.0 g, 29.94 mmol, and 1.0 eq) in dry THF was added methyl magnesium bromide at 0C. The mixture was stirred at RT for 16 h and quenched and extracted as in Intermediate Example 5(c). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 50 % ethyl acetate in hexane). Yield 48.9 % (2.4 g). LC-MS (ESI): Calculated mass: 167.0; Observed massl67.1 [M+H]+ (it: 0.8-1.0 min).
48.9%	In tetrahydrofuran; at 0 - 20℃; for 16h;	To a solution of methyl 3-bromopropanoate (5.0 g,29.94 mmol, and 1.0 eq) in dry THF was added methyl mag21 nesium bromide at 0 C. The mixture was stirred at RT for 16 h and quenched and extracted as in Intermediate Example 5(c). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane). Yield 48.9% (2.4 g). LCMS (ESI): Calculatedmass: 167.0; Observedmass 167.1[M+ H] (it: 0.8-1.0mm).

References: [1]Patent: US2011/105509,2011,A1 .Location in patent: Page/Page column 51.
[2]Patent: US2016/333005,2016,A1 .Location in patent: Paragraph 0074-0075.
[3]Steroids,1991,vol. 56,p. 311 - 315.
[4]Patent: WO2015/105786,2015,A1 .Location in patent: Page/Page column 13; 14.
[5]Patent: WO2013/53983,2013,A1 .Location in patent: Page/Page column 45; 46.
[6]Patent: US2015/11548,2015,A1 .Location in patent: Paragraph 0180.

6
[ 35979-69-2 ]
[ 69739-34-0 ]
[ 116585-11-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 1417 - 1424.
[2]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 828 - 833.

7
[ 35979-69-2 ]
[ 143-33-9 ]
[ 6789-52-2 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

8
[ 35979-69-2 ]
[ 108-98-5 ]
[ 91967-95-2 ]

References: [1]Steroids,1991,vol. 56,p. 311 - 315.

9
[ 110-87-2 ]
[ 35979-69-2 ]
4-bromo-2-methyl-2-butyltetrahydropyranylether [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1995,vol. 30,p. 769 - 778.

10
[ 35979-69-2 ]
[ 107-30-2 ]
[ 305371-69-1 ]

References: [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 525 - 535.

11
[ 863408-15-5 ]
[ 35979-69-2 ]
4-(4-{1-ethyl-1-[4-(3-hydroxy-3-methyl-butylamino)-3-methyl-phenyl]-propyl}-2-methyl-phenylamino)-2-methyl-butan-2-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4327 - 4331.

12
[ 35979-69-2 ]
[ 305371-76-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 525 - 535.

13
[ 35979-69-2 ]
[ 305371-75-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 525 - 535.

14
[ 35979-69-2 ]
[ 66774-84-3 ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 7337 - 7340.

15
[ 35979-69-2 ]
[ 70550-73-1 ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 7337 - 7340.

16
[ 35979-69-2 ]
[ 307953-25-9 ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 7337 - 7340.

17
[ 35979-69-2 ]
[ 139619-77-5 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

18
[ 35979-69-2 ]
[ 139619-79-7 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

19
[ 35979-69-2 ]
[ 139619-76-4 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

20
[ 35979-69-2 ]
[ 139619-80-0 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

21
[ 35979-69-2 ]
[ 194414-15-8 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

22
[ 35979-69-2 ]
[ 139619-81-1 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

23
[ 35979-69-2 ]
[ 139619-75-3 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

24
[ 35979-69-2 ]
[ 139619-73-1 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

25
[ 35979-69-2 ]
[ 139619-84-4 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

26
[ 35979-69-2 ]
[ 194208-59-8 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

27
[ 35979-69-2 ]
[ 139619-83-3 ]

References: [1]Tetrahedron,1997,vol. 53,p. 10851 - 10870.
[2]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

28
[ 35979-69-2 ]
5-ethyl-5-(3-hydroxy-3-methylbutyl)-2-thiobarbituric acid [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1995,vol. 30,p. 769 - 778.

29
[ 35979-69-2 ]
[ 172797-72-7 ]

References: [1]European Journal of Medicinal Chemistry,1995,vol. 30,p. 769 - 778.

30
[ 35979-69-2 ]
[ 139619-82-2 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 105 - 108.

31
methanol potassium hydroxide [ No CAS ]
[ 368878-17-5 ]
[ 35979-69-2 ]
ammonium chloride [ No CAS ]
[ 368878-18-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran;	(5) 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(3-hydroxy-3-methylbutylthiomethyl)androsta-5,7-diene To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(acetylthiomethyl)androsta-5,7-diene (135 mg, 0.223 mmol) and <strong>[35979-69-2]4-bromo-2-methylbutan-2-ol</strong> (186 mg, 1.12 mmol) in tetrahydrofuran (1.5 ml), was added a 1M potassium hydroxide methanol solution (1.5 ml), followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, followed by the addition of a saturated aqueous ammonium chloride solution and the extraction with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent. The thus obtained residue was purified by preparative thin layer chromatography (4 sheets (each 0.5 mm thickness), dichloromethane:ethyl acetate=9:1, developed once) to give the titled compound (131 mg, 90%) as a colorless oil. IR(neat): 3388, 2954, 2929, 2897, 2856, 1462, 1377, 1254, 1099, 1082 cm-1. 1H NMR δ: 0.05 (s, 3H), 0.06 (s, 6H), 0.11 (s, 3H), 0.58 (s, 3H), 0.88 (s, 18H), 0.91 (s, 3H), 1.23 (s, 6H), 2.71 (dd, J=11.8, 5.1 Hz, 1H), 2.75-2.87 (m, 1H), 3.67-3.74 (m, 1H), 3.96-4.12 (m, 1H), 5.28-5.35 (m, 1H), 5.54-5.61 (m, 1H). MS m/z: 648 (M+), 459 (100%). UV λmax nm: 271, 282, 294.

References: [1]Patent: US2003/195176,2003,A1 .

32
methanol potassium hydroxide [ No CAS ]
[ 368877-33-2 ]
[ 35979-69-2 ]
[ 368877-93-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	In tetrahydrofuran;	(1) Synthesis of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(3-hydroxy-3-methylbutylthiomethyl)androsta-5,7,16-triene 17-Acetylthiomethyl-1α,3β-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene (67.7 mg, 0.112 mmol), 1-bromo-3-hydroxy-3-methylbutane (93.5 mg, 0.560 mmol), 1M potassium hydroxide methanol solution (1 ml) and tetrahydrofuran (1 ml) were subjected to reaction using a procedure similar to that of Example 31(1) (at room temperature for 30 min.), worked up and purified by preparative thin layer chromatography (2 sheets (each 0.5 mm thickness), hexane:ethyl acetate=3:1, developed once) to give the titled compound (67.4 mg, 93%) as a colorless oil. IR(neat): 3417, 2956, 2929, 2856, 1471, 1462, 1371, 1254, 1099, 1074 cm-1. 1H NMR δ: 0.05 (s, 3H), 0.07 (s, 3H), 0.07 (s, 3H), 0.11 (s, 3H), 0.85 (s, 3H), 0.88 (s, 9H), 0.89 (s, 9H), 0.95 (s, 3H), 1.24 (s, 6H), 2.59 (m, 2H), 2.85 (m, 1H), 3.23 (m, 2H), 3.71 (brs, 1H), 3.98-4.12 (m, 1H), 5.36-5.42 (m, 1H), 5.56-5.64 (m, 2H). MS m/z: 646 (M+), 457 (100%). UV λmax nm: 271, 281, 294.

References: [1]Patent: US2003/195176,2003,A1 .

33
[ 67883-17-4 ]
[ 35979-69-2 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; chloroform;	Preparation 2 3-Hydroxy-3-methylbutyl phenyl sulphone (Compound 21) To a solution of 4-bromo-2-methyl-2-trimethylsilyloxybutane (9) (12 g) in methanol (55 ml) at room temperature was added ethanolic hydrogen chloride (ca. 1M, 0.2 ml). After 10 minutes the solution was concentrated in vacuo (at room temperature) to constant weight. The residue was taken up in chloroform and reconcentrated to constant weight to give 4-bromo-2-methyl-2-butanol (H, y=1, R1 =R2 =Me) as a chromatographically homogenous oil.

References: [1]Patent: US5401731,1995,A .

34
[ 288-32-4 ]
[ 994-30-9 ]
[ 35979-69-2 ]
[ 617-86-7 ]

Yield	Reaction Conditions	Operation in experiment
4.02 g (93%)	In N,N-dimethyl-formamide; pentane;	EXAMPLE 23 Preparation of 3-bromo-1,1-dimethylpropoxy)triethylsilane To a solution of 2.56 g (15.3 mmol) of <strong>[35979-69-2]4-bromo-2-methyl-2-butanol</strong> and 4.86 g (71.4 mmol) of imidazole in 15 ml of dry N,N-dimethylformamide at 0 C. was added dropwise 6.48 g (43.0 mmol) of chlorotriethylsilane. The mixture was stirred at room temperature for 3 hours and 20 minutes, then quenched by adding ice chips. The mixture was diluted with water and extracted with pentane. The organic phase was washed with water, saturated brine, dried (Na2 SO4) and evaporated to dryness. The residue was chromatographed on silica gel (40-63μ) using pentane to give 4.02 g (93%) of 3-bromo-1,1-dimethylpropoxy)triethylsilane as an oil: IR (CHCl3) 838 cm-1; 1 H NMR (CDCl3) δ 0.58 (q, J=8 Hz, 6 H), 0.94 (t, J=8 Hz, 9 H), 2.03 (m, 2 H), 3.48 (m, 2 H); MS m/e 265 (M+ --CH3).

References: [1]Patent: US5087619,1992,A .

35
ethyl acetate n-hexane [ No CAS ]
[ 539-74-2 ]
[ 35979-69-2 ]

Yield	Reaction Conditions	Operation in experiment
2.57 g (45%)	With hydrogenchloride; methylmagnesium bromide; In tetrahydrofuran;	EXAMPLE 22 Preparation of 4-bromo-2-methyl-2-butanol To a solution of 6.25 g (34.5 mmol) of ethyl 3-bromopropionate in 28 ml of dry tetrahydrofuran at -20 C. was added dropwise 28.8 ml (80.6 mmol) of 2.8M methylmagnesium bromide in ether. The mixture was stirred at room temperature for 2 hours and 50 minutes then quenched by addition of 15 ml of saturated aqueous ammonium chloride. After addition of 42 ml of 1N aqueous HCl, the organic phase was separated and the aqueous phase extracted with ether. The combined organic extracts were washed with saturated brine, dried (Na2 SO4) and evaporated to dryness. The residue was chromatographed on silica gel (40-63μ) using 30% ethyl acetate-hexane to give 2.57 g (45%) of 4-bromo-2-methyl-2-butanol as an oil: IR (CHCl3) 3605 cm-1; 1 H NMR (CDCl3) δ1.27 (s, 6 H), 1.33 (s, 1 H), 2.11 (m, 2 H), 3.51 (m, 2 H); MS m/e 151 (M+ --CH3).

References: [1]Patent: US5087619,1992,A .

36
[ 210218-50-1 ]
[ 35979-69-2 ]
[ 210218-51-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium hydroxide; In tetrahydrofuran; methanol;	Example 3 Preparation of 1α-(tert-butyldimethylsilyloxy)-3βhydroxy-20(S)-(3-hydroxy-3-methylbutylthio)pregna-5,7,16-triene To a solution of 1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-phenoxycarbonylthiopregna-5,7,16-triene (81.6 mg, 0.140 mmol) and <strong>[35979-69-2]4-bromo-2-methyl-2-butanol</strong> (117 mg, 0.700 mmol) in tetrahydrofuran (1 ml) was added 1M KOH solution in methanol (1 ml), and the mixed solution was stirred at room temperature for 30 minutes, then concentrated under reduced pressure. The residue was diluted with hexane, washed with brine and dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by preparative thin layer chromatography (0.5 mm*2, dichloromethane:ethyl acetate=8:1, developed once) to give the title compound as a colorless oil (60.3 mg, 79%). IR(neat): 3400, 2950, 2850, 1460, 1370, 1250, 1200, 1150, 1060 cm-1. 1H NMR δ: 0.08(s, 3H), 0.13(s, 3H), 0.88(s, 9H), 0.93(s, 3H), 0.94(s, 3H), 1.22(s, 6H), 1.43(d, J=6.9 Hz, 3H), 3.51(q, J=6.9 Hz, 1H), 3.75(brs, 1H), 3.95-4.17(m, 1H), 5.37-5.45(br, 1H), 5.59-5.69(br, 2H). MS m/z: 546 (M+), 278 (100%). UV λmax nm: 270, 281, 293.

References: [1]Patent: US6184398,2001,B2 .

37
[ 748184-71-6 ]
[ 35979-69-2 ]
(R)-4-butoxy-N-(3-fluoro-4-[3-[(3-hydroxy-3-methylbutyl)-methylamino]-pyrrolidin-1-yl]-phenyl)-N-methylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethyl acetate; N,N-dimethyl-formamide;	Example 249 R-4-Butoxy-N-(3-fluoro-4-{3-[(3-hydroxy-3-methylbutyl)methylamino]pyrrolidin-1-yl}-phenyl)-N-methylbenzamide A solution of (R)-4-butoxy-N-[3-fluoro-4-(3-methylaminopyrrolidin-1-yl)phenyl]benzamide (0.03 g), triethylamine (0.02 g) and <strong>[35979-69-2]4-bromo-2-methylbutan-2-ol</strong> (0.03 g) in DMF (2 ml) was heated at 80 C. for 16 hours. After cooling, ethyl acetate (100 ml) was added, the mixture was washed with water (2*50 ml), and the organic phase was dried with sodium sulfate, filtered and concentrated. The residue was purified by preparative HPLC. This resulted in the product with the molecular weight of 471.62 (C27H38FN3O3); MS (ESI): 472 (M+H+).

References: [1]Patent: US2004/220191,2004,A1 .

38
[ 539-74-2 ]
[ 35979-69-2 ]

Yield	Reaction Conditions	Operation in experiment
	With methylmagnesium bromide; In diethyl ether;	4-Bromo-2-methylbutan-2-ol Methylmagnesium bromide (3M in diethyl ether, 46 ml) was added to a solution of ethyl 3-bromopropionate (10 g) in diethyl ether (100 ml) at room temperature under argon. During this, the mixture was kept at above 20 C. and below 35 C. After 2 hours, the mixture was poured into a saturated ammonium chloride solution. This was followed by extraction with diethyl ether, drying with sodium sulfate, filtration and concentration. This resulted in the desired product.

References: [1]Patent: US2004/220191,2004,A1 .

39
[ 35979-69-2 ]
[ 75-36-5 ]
[ 1134111-92-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 0℃;	Example M44: 1-Methylcyclopropyl 4-((5-(4-(3-acetoxy-3- methylbutylsulfonyl)piperazin-l-yl)pyrazin-2-yloxy)methyl)piperidine-l- carboxylate.Br Step A AcO Br Step B AcO SAc M 44a M44b M44c[00272] Step A: A solution of M44a (1.48 g, 8.9 mmol) in dichloromethane (49 mL) is cooled in an ice/water bath and treated with pyridine (913 mg, 12mmol) and acetyl chloride (868 mg, 11 mmol) and the reaction is allowed to stir overnight as the ice bath melts. The reaction is then quenched with water. The organic phase is isolated, dried over MgSO4, filtered, evaporated and the residue is purified on silica gel using a linear gradient of 0-100% ethyl acetate in hexane to afford M44b; A satisfactory ESIMS could not be obtained.

References: [1]Patent: WO2009/38974,2009,A1 .Location in patent: Page/Page column 124.

40
[ 35979-69-2 ]
[ 868963-98-8 ]
[ 1256957-92-2 ]

Yield	Reaction Conditions	Operation in experiment
42%		To a solution of 2-amino-5-bromopyridine-3-sulfonyl chloride (reagent preparation 25, step 1) (0.40 g, (1.47 mmol) in a mixture of 1 ,4-dioxane (8.0 mL) and water (1.0 mL) was added triphenylphosphine (1.64 g, 6.25 mmol) and the reaction mixture was stirred for 50 minutes at room temperature. Potassium carbonate (0.35 g, 2.50 mmol) was introduced, followed by <strong>[35979-69-2]4-bromo-2-methyl-2-butanol</strong> (Tetrahedron Letters 2000, 41(38), 7337-7340) (0.31 g, 1.86 mmol) and the reaction mixture was stirred at 80 C for 16 hours. After cooling to room temperature the reaction mixture was concentrated and the residue was partitioned between brine (50 mL) and ethyl acetate (100 mL). The organic layer was separated and washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated. Gradient flash chromatography (25% to 50% ethyl acetate in hexane) provided 4-[(2-amino-5-bromopyridin-3-yl)thio]-2-methylbutan-2-ol (0.18 g, 42%); MS (EI) for C10H15BrN2OS: 292 (MH+).

References: [1]Patent: WO2010/135524,2010,A1 .Location in patent: Page/Page column 245.

41
[ 35979-69-2 ]
[ 1297282-75-7 ]
[ 1297284-62-8 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 90℃;Inert atmosphere;	To a 100 mL round bottom flask was added intermediate 5, tert-butyl 2-(5-fluoro-3-(4-hydroxyphthalazin-1-yl)-2-methyl-1H-indol-1-yl)acetate (0.500 g, 1.23 mmol, 1.0 eq.), cesium carbonate (1.00 g, 3.07 mmol, 2.5 eq.) and DMF (12 mL, 0.1 M). The flask was purged with nitrogen and intermediate 136 (0.615 g, 3.68 mmol, 3.0 eq.) was added and the reaction stirred at 90 C. overnight. The reaction was cooled to room temperature, extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated in vacuo. The resulting material was carried on crude.

References: [1]Patent: US2011/105509,2011,A1 .Location in patent: Page/Page column 51.

42
[ 35979-69-2 ]
4-(7-(3'-fluoro-6'-methyl-2,2'-bipyridin-4-ylamino)-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylbutan-2-ol trifluoroacetate [ No CAS ]

References: [1]Patent: WO2011/146287,2011,A1 .
[2]Patent: WO2011/146287,2011,A1 .

43
[ 35979-69-2 ]
4-(7-(3'-fluoro-5,6'-dimethyl-2,2'-bipyridin-4-ylamino)-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylbutan-2-ol trifluoroacetate [ No CAS ]

References: [1]Patent: WO2011/146287,2011,A1 .
[2]Patent: WO2011/146287,2011,A1 .

44
[ 35979-69-2 ]
4-(7-(3'-fluoro-6'-methyl-2,2'-bipyridin-4-ylamino)-1H-pyrazolo[4,3-b]pyridin-1-yl)-2-methylbutan-2-ol [ No CAS ]

References: [1]Patent: WO2011/146287,2011,A1 .

45
[ 35979-69-2 ]
[ 1350648-20-2 ]
[ 1350649-19-2 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 1h;Microwave irradiation;	[0353] 7-Iodo-2H-pyrazolo[4,3-b]pyridine (342 mg, 1.396 mmol), 4-bromo-2-methylbutan- 2-ol (233 mg, 1.396 mmol) and CS2CO3 (455 mg, 1.396 mmol) were combined in DMF (5 mL) and heated in a microwave at 120 C for 60 minutes. The reaction was cooled, filtered, and concentrated to give a residue which was purified by silica column eluted using a step gradient of EtOAc (0-90%) in hexanes to give 4-(7-iodo-2H-pyrazolo[4,3-b]pyridin-2-yl)-2- methylbutan-2-ol.

References: [1]Patent: WO2011/146287,2011,A1 .Location in patent: Page/Page column 109.

46
[ 35979-69-2 ]
[ 1350648-20-2 ]
[ 1350649-19-2 ]
[ 1350649-20-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 1h;Microwave irradiation;	[0350] 7-Iodo-2H-pyrazolo[4,3-b]pyridine (342 mg, 1.396 mmol), 4-bromo-2-methylbutan- 2-ol (233 mg, 1.396 mmol) and CS2CO3 (455 mg, 1.396 mmol) were combined in DMF (5 mL) and heated in a microwave at 120 C for 60 minutes. The reaction was cooled, filtered, and concentrated to give a residue which purified on a silica column and eluted using a step gradient of EtOAc (0-90%) in hexanes to give 4-(7-iodo-2H-pyrazolo[4,3-b]pyridin-2-yl)-2- methylbutan-2-ol and 4-(7-iodo-lH-pyrazolo[4,3-b]pyridin-l-yl)-2-methylbutan-2-ol.

References: [1]Patent: WO2011/146287,2011,A1 .Location in patent: Page/Page column 108.

47
[ 35979-69-2 ]
[ 1350648-20-2 ]
[ 1350649-20-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.666667h;Microwave irradiation;	[0379] 7-Iodo-2H-pyrazolo[4,3-b]pyridine (357 mg, 1.457 mmol), 4-bromo-2-methylbutan- 2-ol (243 mg, 1.457 mmol) and Cs2C03 (475 mg, 1.457 mmol) were combined in DMF (5 mL) and heated in a microwave at 120 C for 40 minutes. The reaction was then cooled, filtered, and concentrated to give a residue which was purified by silica chromatography eluted with a step gradient of EtOAc in hexanes to give 4-(7-iodo-lH-pyrazolo[4,3- b]pyridin-l-yl)-2-methylbutan-2-ol which was dried and used immediately.

References: [1]Patent: WO2011/146287,2011,A1 .Location in patent: Page/Page column 117-118.

48
[ 35979-69-2 ]
[ 1350648-20-2 ]
4-(7-(3'-fluoro-6'-methyl-2,2'-bipyridin-4-ylamino)-1H-pyrazolo[4,3-b]pyridin-1-yl)-2-methylbutan-2-ol [ No CAS ]

References: [1]Patent: WO2011/146287,2011,A1 .

49
[ 35979-69-2 ]
[ 1397692-47-5 ]

References: [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 828 - 833.

50
[ 35979-69-2 ]
[ 876732-44-4 ]

Yield	Reaction Conditions	Operation in experiment
0.2 g	With Caswell No. 744A; triethylamine; In dichloromethane; water monomer;	b) 4-Azido-2-methylbutan-2-olTo a mixture of <strong>[35979-69-2]4-bromo-2-methylbutan-2-ol</strong> (0.4 g. , 2.4 mmol) and triethylamine (1 ml, 7 mmol, 3 eq.) in CH2C12 (15 ml) was added sodium azide (0.47 g, 7 mmol, 3 eq.) in H20 (5 ml) and the mixture was allowed to stir overnight. The mixture was quenched with water and extracted with CH2C12 (3 * 50 ml). The combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the product in 65 % yield (0.2 g). Ή NMR (300 MHz, DMSO-i4): δ 4.39 (br s, 1H), 3.40-3.32 (m, 2H), 1.15 (t, 2H), 1.23-1.04 (m, 6H).
0.2 g	With Caswell No. 744A; triethylamine; In dichloromethane; water monomer;	To a mixture of <strong>[35979-69-2]4-bromo-2-methylbutan-2-ol</strong> (0.4 g, 2.4 mmol) and triethylamine (1 ml, 7 mmol, 3 eq.) in CH2Cl2 (15 ml) was added sodium azide (0.47 g, 7 mmol, 3 eq.) in H2O (5 ml) and the mixture was allowed to stir overnight. The mixture was quenched with water and extracted with CH2Cl2 (3*50 ml). The combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the product in 65% yield (0.2 g). 1H NMR (300 MHz, DMSO-d6): δ 4.39 (br s, 1H), 3.40-3.32 (m, 2H), 1.15 (t, 2H), 1.23-1.04 (m, 6H).

References: [1]Journal of Medicinal Chemistry,2022,vol. 65,p. 4767 - 4782.
[2]Patent: WO2013/53983,2013,A1 .Location in patent: Page/Page column 32.
[3]Patent: US2015/11548,2015,A1 .Location in patent: Paragraph 0139.

51
[ 2075-45-8 ]
[ 35979-69-2 ]
[ 1430727-38-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;	b) 4-(4-Bromo- 1 H-pyrazol- 1 -yl)-2-methylbutan-2-olTo a solution of 4-bromo-lH-pyrazole (1 g, 6.84 mmol, 1.0 eq) in DMF were added K2C03 (2.3 g, 17.1 mmol, 2.5 eq.) and <strong>[35979-69-2]4-bromo-2-methylbutan-2-ol</strong> (1.7 g, 10.27 mmol, 1.5 eq.). The mixture was stirred at RT for 16 h. The mixture was quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off to afford the product in 60 % yield (0.9 g). LC-MS (ESI): Calculated mass 233.0; Observed mass 235.0.[M+H]+ (rt: 0.64 min).
60%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;	To a solution of 4-bromo-1H-pyrazole (1 g, 6.84 mmol, 1.0 eq) in DMF were added K2CO3 (2.3 g, 17.1 mmol, 2.5 eq.) and <strong>[35979-69-2]4-bromo-2-methylbutan-2-ol</strong> (1.7 g, 10.27 mmol, 1.5 eq.). The mixture was stirred at RT for 16 h. The mixture was quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off to afford the product in 60% yield (0.9 g). LC-MS (ESI): Calculated mass 233.0; Observed mass 235.0. [M+H]+ (rt: 0.64 min).

References: [1]Patent: WO2013/53983,2013,A1 .Location in patent: Page/Page column 46.
[2]Patent: US2015/11548,2015,A1 .Location in patent: Paragraph 0181.

52
[ 35979-69-2 ]
[ 1354494-81-7 ]
[ 1354495-48-9 ]

Yield	Reaction Conditions	Operation in experiment
47%	With caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 1h;	To a solution of 300 mg (0.462 mmol) of (-)-4-(4,4-difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-hydroxypyrimidin-2-yl)piperidin-4-yl]-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Example 4, in 2.3 ml of N,N-dimethylformamide, 301 mg (0.924 mmol) of cesium carbonate and 93 mg (0.55 mmol) of <strong>[35979-69-2]4-bromo-2-methylbutan-2-ol</strong>, which was synthesized by the method described in Yagamare Fall et al., Tetrahedron Letters, 2000, Vol. 41, pp. 7337-7340, were added, and the reaction solution was stirred at 50 C. for 1 hour. After completion of the reaction, water was poured into the reaction solution and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=70/30-50/50 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure. n-Hexane was added to the obtained residue and the precipitate was obtained by filtration to provide 161 mg of the title compound as a white powder (yield: 47%). Specific optical rotation: [α]D20=-72.2 (C=1.03, chloroform). 1H-NMR spectrum (300 MHz, CDCl3) δ: 8.04 (2H, s), 7.63 (2H, d, J=8 Hz), 7.36 (2H, d, J=8 Hz), 7.20 (1H, d, J=46 Hz), 5.12 (1H, dt, J=6, 6 Hz), 4.74-4.61 (1H, m), 4.46-4.33 (1H, m), 4.11 (2H, t, J=6 Hz), 3.70-3.54 (1H, m), 2.91-2.58 (4H, m), 2.40-1.62 (18H, m), 1.30 (6H, s), 1.15 (3H, s), 1.00 (3H, s), 0.68-0.58 (1H, m). Mass spectrum (EI, m/z): 734 [M+].

References: [1]Patent: US2013/109653,2013,A1 .Location in patent: Paragraph 0599-0603.

53
[ 35979-69-2 ]
C₆H₉BrN₄ [ No CAS ]
C₁₁H₁₉BrN₄O [ No CAS ]

References: [1]MedChemComm,2013,vol. 4,p. 422 - 431.

54
[ 35979-69-2 ]
C₈H₁₁BrN₄ [ No CAS ]
C₁₃H₂₁BrN₄O [ No CAS ]

References: [1]MedChemComm,2013,vol. 4,p. 422 - 431.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • General Reactivity • Grignard Reaction • Heat of Combustion • Hiyama Cross-Coupling Reaction • Hydride Reductions • Jones Oxidation • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Swern Oxidation

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CAS No.: 35979-69-2

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CAS No.: 35979-69-2

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