[ CAS No. 308283-47-8 ] {[proInfo.proName]}

Name: 308283-47-8|3-Bromo-N-(tert-butyl)benzenesulfonamide|98%
Brand: Ambeed
SKU: A198998
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Quality Control of [ 308283-47-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 308283-47-8 ]

Product Details of [ 308283-47-8 ]

CAS No. :	308283-47-8	MDL No. :	MFCD07363824
Formula :	C₁₀H₁₄BrNO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PKTQHWKZGFKXGT-UHFFFAOYSA-N
M.W :	292.19	Pubchem ID :	4820926
Synonyms :

Calculated chemistry of [ 308283-47-8 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.4
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	64.5
TPSA :	54.55 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.35
Log Po/w (XLOGP3) :	2.74
Log Po/w (WLOGP) :	3.61
Log Po/w (MLOGP) :	2.29
Log Po/w (SILICOS-IT) :	1.75
Consensus Log Po/w :	2.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.48
Solubility :	0.0977 mg/ml ; 0.000334 mol/l
Class :	Soluble
Log S (Ali) :	-3.54
Solubility :	0.0843 mg/ml ; 0.000288 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.43
Solubility :	0.0109 mg/ml ; 0.0000372 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.39

Safety of [ 308283-47-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338-P280	UN#:	N/A
Hazard Statements:	H319-H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 308283-47-8 ]

* 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 [ 308283-47-8 ]

[ 308283-47-8 ] Synthesis Path-Downstream 1~43

1
[ 2905-24-0 ]
[ 75-64-9 ]
[ 308283-47-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane; at 0 - 20℃; for 0.5h;	To a solution of ie/t-butylamine (9.74 g, 14 mL, 133.23 mmol) in DCM (100 mL) at 0 C was added 3-bromobenzenesulfonyl chloride (11.37 g, 6.4 mL, 44.52 mmol) After 10 min., the cooling bath was removed and the mixture was stirred at room temperature for 20 min. Aqueous 1 N HC1 (100 mL) was added and the phases were separated. The organic layer was washed with water (100 mL) and dried with MgS04, filtered and concentrated in vacuo to afford 3-bromo- V-ieri-butyl-benzenesulfonamide (12.38 g, 95%) as a white solid. 1H NMR (400 MHz, CDCL) d 8.05 (t, J = 1.7 Hz, 1H), 7.83 (d, J = 7.6 Hz, 1H), 7.67 (d, J = 7.7 Hz, 1H), 7.38 (t, J = 7.9 Hz, 1H), 4.71 (br s, 1H), 1.26 (s, 9H). ESI-MS m/z calc. 290.9929, found 236.0 (M-C4H8+H)+; Retention time: 1.79 minutes (LC method E).
93%	In tetrahydrofuran;	Step 1 3-(tert-butylaminosulfonyl) phenylbromide To a 0 C. solution of 3-bromobenzenesulfonyl chloride (3.6 g, 11.7 mmol) in 10 mL of THF, was added 2.7 mL (25.8 mmol) of t-butylamine. The solution was stirred at room temperature for 1 h and diluted with ethyl acetate. The organic layer was washed with 1 N HCl, water and with brine, dried over MgSO4 and concentrated under reduced pressure. The bromide (3.86 g, 93%) was obtained as a white solid.
	With triethylamine; In dichloromethane; for 1h;	tert-Butylamine (3.14 g, 3.0 mmol, 1. 1 eq) and triethylamine (5.94 g, 58.6 mmol, 1.5 eq. ) were dissolved in dichloromethane (20 mL) and stirred at room temperature while 3-bromobenzenesulfonyl chloride (10.0 g, 39.1 mmol) was added slowly. The mixture was stirred for 1 hour and then concentrated by evaporation under reduced pressure. The residue was taken up in 5% citric acid and ethyl acetate. The organic layer is washed repeatedly with brine and water, dried over anhydrous magnesium sulfate and concentrated to give N-TERT-BUTYL-3-BROMOBENZENESULFONAMIDE (10.94 g) as a white powder

	With triethylamine; In dichloromethane; at 20℃; for 1h;	TERT-BUTYLAMINE (3.14 G, 3.0 MMOL, 1.1 EQ. ) AND TRIETHYLAMINE (5.94 G, 58.6 MMOL, 1.5 EQ.) were dissolved in dichloromethane (20 mL) and the solution was stirred at room temperature while 3-bromobenzenesulfonyl chloride (10.0 g, 39.1 mmol) was added slowly. The mixture was stirred for 1 hour and then concentrated by evaporation under reduced pressure. The residue is taken up in 5% citric acid and ethyl acetate. The organic layer was washed repeatedly with brine and water and dried over anhydrous magnesium sulfate. Evaporation of the filtrate gave N-TERT-BUTYL-3-BROMOBENZENESULFONAMIDE as a white powder (10.94 g).
	In 1,4-dioxane; at 20℃; for 1h;	Step 1. A mixture of 3-bromobenzene-l-sulfonyl chloride (2 g, 7.83 mmol, 1.0 eq) and 2- methylpropan-2-amine (1.72 g, 23.5 mmol, 3.0 eq) in dioxane (50 mL) was stirred at room temperature for 1 hours and filtered. The filtrate was concentrated in vacuo to afford 3-bromo-N- tert-butylbenzenesulfonamide (all for the next step). LCMS: 291.9, 293.9 [M+H]+.

Reference： [1]Patent: WO2019/195739,2019,A1 .Location in patent: Paragraph 00216
[2]Patent: US6316472,2001,B1
[3]Patent: WO2004/50637,2004,A2 .Location in patent: Page 75
[4]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6841 - 6849
[5]Patent: WO2004/62661,2004,A1 .Location in patent: Page/Page column 30
[6]Patent: WO2011/19405,2011,A1 .Location in patent: Page/Page column 117

3
[ 308283-47-8 ]
[ 14394-70-8 ]
[ 936092-53-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; for 3h;Heating / reflux;	[0178] A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.4 g, 2.8 mmol), 3-bromo- iV-te/t-butyl-benzenesulfonamide (1.0 g, 3.4 mmol), Pd2(dba)3 (0.17 g, 0.19 mmol), Xantphos (0.2 g, 3.5 mmol) and cesium caibonate (2.0 g, 6.1 mmol) was suspended in dioxane (25 mL) and heated at reflux under the argon atmosphere for 3 h. The reaction mixture was cooled to room temperature and diluted with DCM (30 mL). The mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc and hexanes added until solid precipitated. After filtration, the title compound (1.2 g, 98percent) was obtained as a light brown solid. It was used in the next step without purification. MS (ES+): m/z 355 (M+H)+.
98%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; for 3h;Inert atmosphere; Reflux;	Example 4.1(a)Intermediate[0135] A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (1) (0.4 g, 2.8 mmol), 3-bromo- /V-ieri-butyl-benzenesulfonamide (2) (1.0 g, 3.4 mmol), Pd2(dba)3 (0.17 g, 0.19 mmol), Xantphos (0.2 g, 3.5 mmol) and cesium carbonate (2.0 g, 6.1 mmol) was suspended in dioxane (25 mL) and heated at reflux under the argon atmosphere for 3 h. The reaction mixture was cooled to room temperature and diluted with DCM (30 mL). The mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc and hexanes added until solid precipitated. After filtration, the title compound (1.2 g, 98percent) was obtained as a light brown solid. It was used in the next step without purification. MS (ES+): m/z 355 (M+H)+.

Reference： [1]Patent: WO2007/53452,2007,A1 .Location in patent: Page/Page column 109
[2]Patent: WO2012/60847,2012,A1 .Location in patent: Page/Page column 42

4
[ 308283-47-8 ]
[ 936092-52-3 ]
TG₁₀₁₂₀₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 1650℃; for 0.333333h;Microwave irradiation;	[0176] A suspension of intermediate 32 (0.30 g, 1.0 mmol), 3-bromo-iV-tert-butyl- benzenesulfonamide (0.35 g, 1.2 mmol), Pd2(dba)3 (60 mg, 0.066 mmol), Xantphos (70 nig, 0.12 mmol) and cesium carbonate (0.70 g, 2.1 mmol) in dioxane/DMF (3/1, 8 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 "C for 20 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by HPLC. The fractions were combined and poured into saturated NaHCO3 solution (40 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue triturated in a mixture of EtOAc/hexanes (1/7, 40 mL). After filtration, the title compound was obtained as an off white solid (0.30 g, 59percent).[0177] 1H NMR (500 MHz, DMSO-d6): delta 1.12 (s, 9H), 2.11 (s, 3H), 2.22 (s, 3H), 2.45 (t, J= 4.7 Hz, 4H), 3.02 (t, J- 4.8 Hz, 4H), 6.81 (d, J= 9.1 Hz, 2H), 7.45-7.52 (m, 4H), 7.56 (s, IH), 7.89 (s, IH), 8.10-8.16 (m, 2H), 8.51 (s, IH), 8.70 (s, IH) MS (ES+): m/z 510 (M+H)+.

Reference： [1]Patent: WO2007/53452,2007,A1 .Location in patent: Page/Page column 108-109

5
[ 308283-47-8 ]
[ 936092-54-5 ]
N-tert-butyl-3-{5-methyl-2-[3-(piperidine-1-sulfonyl)-phenylamino]-pyrimidin-4-ylamino}-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; N,N-dimethyl-formamide; at 160℃; for 0.25h;Microwave irradiation;	[0190] A suspension of intermediate 34 (0.10 g, 0.29 mmol), 3-bromo-iV-2rt-butyl- benzenesulfonamide (84 mg, 0.29 mmol), Pd2(dba)3 (15 mg, 0.016 mmol), Xantphos (20 mg, 0.035 mmol) and cesium carbonate (0.18 g, 0.55 mmol) in dioxane/DMF (3/1, 4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 "C for 15 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by HPLC. The fractions were combined and poured into saturated NaHCO3 solution (30 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The <n="116"/>filtrate was concentrated and the residue dissolved in minimum amount of EtOAc and liexanes added until solid precipitated. After filtration, the title compound was obtained as a white solid (20 mg, 12percent) .[0191] 1H NMR (500 MHz, DMSO-d6): delta 1.12 (s, 9H), 1.30-1.40 (m, 2H), 1.50-1.56 (m, 4H), 2.16 (s, 3H), 2.88 (t, J= 5.3 Hz, 4H), 7.17 (d, J= 7.8 Hz, IH), 7.43 (t, J= 8.0 Hz, IH), 7.59-7.60 (m, 2H), 7.58 (s, IH), 8.13 (s, IH), 7.16 (dd, J= 7.9, 1.9 Hz, IH), 8.18-8.22 (m, IH), 8.67 (s, IH), 9.37 (s, IH). MS (ES+): m/z 559 (M+H)+.

Reference： [1]Patent: WO2007/53452,2007,A1 .Location in patent: Page/Page column 114

6
[ 308283-47-8 ]
[ 936092-55-6 ]
N-tert-butyl-3-{5-methyl-2-[3-(4-methyl-piperazine-1-sulfonyl)-phenylamino]-pyrimidin-4-ylamino}-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; N,N-dimethyl-formamide; at 160℃; for 0.25h;Microwave irradiation;	[0199] A suspension of intermediate 35 (0.10 g, 0.28 mmol), 3-bromo-iV-fert-butyl- benzenesulfonamide (80 mg, 0.27 mmol), Pd2(dba)3 (15 mg, 0.016 mmol), Xantphos (20 mg, 0.035 mmol) and cesium carbonate (0.18 g, 0.55 mmol) in dioxane/DMF (3/1, 4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 °C for 15 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by HPLC. The fractions were combined and poured into saturated NaHCO3 solution (30 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The <n="120"/>filtrate was concentrated and the residue dissolved in minimum amount of EtOAc and hexanes added until solid precipitated. After filtration, the title compound was obtained as a white solid (10 mg, 6percent).[0200] 1H NMR (500 MHz, DMSO-d6): delta 1.12 (s, 9H), 2.13 (s, 3H), 2.16 (s, 3H), 2.33- 2.40 (m, 4H), 2.85-2.94 (m, 4H), 7.18 (d, J= 8.1 Hz, IH), 7.44 (t, J= 8.0 Hz, IH), 7.49-7.54 (m, 2H), 7.58 (s, IH), 8.00-8.03 (m, 2H), 8.13 (s, IH), 8.15 (dd, J= 8.6, 1.6 Hz, IH), 8.18- 8.23 (m, IH), 8.66 (s, IH), 9.38 (s, IH). MS (ES+): m/z 574 (M+H)+.

Reference： [1]Patent: WO2007/53452,2007,A1 .Location in patent: Page/Page column 118-119

7
[ 308283-47-8 ]
[ 936092-66-9 ]
N-tert-butyl-3-[5-methyl-2-(3-morpholin-4-ylmethyl-phenylamino)-pyrimidin-4-ylamino]-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane;Heating / reflux;	[0288] A suspension of intermediate 50 (1.0 g, 3.42 mmol), 3 -bromo-iV- tot-butyl - benzenesulfonamide (1.28 g, 4.28 mmol), Pd2(dba)3 (30 nag, 0.03 mmol), Xantphos (40 mg, 0.07 mmol) and cesium carbonate (3.34 g, 10.24 mmol) in dioxane (50 mL) was degassed with argon for 2 min then refluxed for overnight. After cooling to room temperature, the solvent was removed by rotovap and the resulting mixture was purified by silica gel with 10percent CH3OH/CHCI3 as an eluent to afford the title compound as a white solid. The white was dissolved in hot dioxane (150 mL) and titrated with 2 M HCl in dioxane to pH 1. The solvent was removed by rotovap and the solid was recrystalized from methanol (0.15 g, 8percent).[0289] 1H NMR (500 MHz, DMSOd6): 1.08 (s, 9H), 2.20 (s, 3H), 3.0-3.2 (m, 4H), 3.7- 4.0 (m, 4H), 4.23 (s, 2H)5 7.33 (t, J= 7.9 Hz, IH), 7.38 (d, J= 7.7 Hz, IH), 7.48 (s, IH), 7.55-7.65 (m, 3H), 7.71 (d, J= 7.9 Hz, IH), 7.90 (d, J= 7.4 Hz, IH), 8.01 (s, IH), 9.96 (br s, IH)5 10.61 (br s, IH), 11.31 (br s, IH). MS (ES+): m/z 511 (M+H)+.

Reference： [1]Patent: WO2007/53452,2007,A1 .Location in patent: Page/Page column 150-151

8
[ 308283-47-8 ]
[ 926-62-5 ]
[ 1059104-16-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6841 - 6849

9
[ 308283-47-8 ]
[ 6921-34-2 ]
[ 1059104-19-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6841 - 6849

10
[ 308283-47-8 ]
[ 73183-34-3 ]
[ 706820-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 90℃; for 2h;Inert atmosphere;	Step 2. A flask charged with <strong>[308283-47-8]3-bromo-N-tert-butylbenzenesulfonamide</strong> obtained in step 1 (2.3 g, 7.83 mmol, 1.0 eq), pinacol-dibrane (3.98 g, 15.66 mmol, 2.0 eq), KOAc (2.31 g, 23.49 mmol, 3.0 eq) and Pd (dppf)2Cl2 (640 mg, 0.78 mmol, 0.1 eq) was flushed with nitrogen followed by the addition of 1 ,4-dioxane (20 mL). The mixture was stirred and heated to 9O0C for 2 hours, cooled to room temperature and diluted with EtOAc. The mixture was filtered over a pad of silica gel. The filtrate was concentrated. To the residue, petroleum ether was added. The emerged solid was filtered off. The filtrate was concentrated. The residue was purified by silica gel chromatography to give N-tert-butyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzenesulfonamide (2.32 g, 90% over 2 steps). LC-MS (m/z) - 284.1 [M-56+H]+.

Reference： [1]Patent: WO2011/19405,2011,A1 .Location in patent: Page/Page column 117

11
[ 308283-47-8 ]
[ 1310496-34-4 ]

Reference： [1]Patent: WO2011/19405,2011,A1

12
[ 308283-47-8 ]
[ 14394-70-8 ]
N-tert-butyl-3-{5-methyl-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-pyrimidin-4-ylamino}-benzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2012/60847,2012,A1

13
[ 308283-47-8 ]
[ 1229979-94-5 ]
N-(tert-butyl)-3-((5-cyano-2-((4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; N,N-dimethyl-formamide; for 48h;Reflux; Inert atmosphere;	General procedure: [00416] A mixture of 4-amino-2-((4- (4-methylpiperazin- 1 -yl)phenyl)amino)pyrimidine-5- carbonitrile (1 mol equiv), 3-bromo-N-(tert-butyl)-5-substiteud benzenesulfonamide (1.2 mol equiv), tris(dibenzylideneacetone)dipalladium(0) (0.05 mol equiv), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.1 mol equiv), cesium carbonate (2 mol equiv) were suspended in 1,4-dioxane (0.17 M) and N,N-dimethylmethanamide (0.5 M) and heated at reflux under the nitrogen atmosphere for 48 hours. The reaction mixture was cooled to room temperature and poured into water. The mixture was extracted with ethyl acetate, washed with brine. The extract was dried over sodium sulfate, filtrated, and concentrated in vacuo. The residue was purified by flash column chromatography (hexane - ethyl acetate) to afford the title compound.[00417] Yield 19percent. Pale yellow amorphous solid. ?H NMR (400 MHz, DMSO-d6) S ppm1.10 (s, 9 H) 2.21 (s, 3 H) 2.40-2.47 (m, 4 H) 3.01 - 3.11 (m, 4 H) 6.85 (d, J=9.00 Hz, 2 H)7.21 - 7.43 (m, 3 H) 7.47 - 7.65 (m, 3 H) 8.29 (s, 1 H) 9.32 - 9.52 (m, 2 H). MS (ESI) mlz:521 (M+H).

Reference： [1]Patent: WO2015/117053,2015,A1 .Location in patent: Paragraph 00416; 00417

14
[ 308283-47-8 ]
[ 75-77-4 ]
N-tert-butyl-3-trimethylsilyl-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Under argon atmosphere, H-butyllithium (2.5 M in hexanes, 4.5 mL, 11.25 mmol) was added dropwise to a solution of 3-bromo-/V-ie/+-butyl-benzenesulfonamide (1.5 g, 5.1336 mmol) in tetrahydrofuran (15.0 mL) at -100 C. The mixture was stirred at this temperature for 30 minutes. Trimethylsilyl chloride (1.284 g, 1.5 mL, 11.82 mmol) was added dropwise at -100 C. The mixture was warmed up to room temperature and hydrolyzed with an aqueous hydrochloric acid solution (25 mL, 6 N). The layers were separated and the organic solution was washed with a saturated aqueous ammonium chloride solution (5 x 25 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated to afford crude /V-ie/+-butyl-3-trimethylsilyl-benzenesulfonamide (1.4 g, 67%) as a colorless oil. [00218] Three different lots of material were prepared using similar conditions. The three lots of impure /V-ie/+-butyl-3-trimethylsilyl-benzenesulfonamide (3.94 g, 8.28 mmol) were combined together and purified by flash chromatography (loaded in heptanes) (120+25 g S1O2, eluting 0 to 20% ethyl acetate in heptanes). The product fractions were combined and concentrated in vacuo to give /V-ie/+-butyl-3-trimethylsilyl- benzenesulfonamide (2.87 g, 107%) as a colorless oil. 'H NMR (400 MHz, CDCL) d 8.03 (s, 1H), 7.90 - 7.84 (m, 1H), 7.67 (d, J = 7.3 Hz, 1H), 7.46 (t, J = 7.6 Hz, 1H), 4.64 (s, 1H), 1.24 (s, 9H), 0.30 (s, 9H).

Reference： [1]Patent: WO2019/195739,2019,A1 .Location in patent: Paragraph 00217-00218

15
[ 308283-47-8 ]
[ 1066-37-1 ]
N-tert-butyl-3-trimethylgermyl-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		A solution of 3-bromo-/V-/eri-butyl-benzenesulfonamide (1.7 g, 5.82 mmol) in THF (35 mL) was chilled to -95 C, then a solution of H-butyllithium in hexane (5.4 mL of 2.5 M, 13.50 mmol) was added drop-wise over ten minutes. The pale yellow solution was stirred for thirty minutes at -95 C, then trimethylgermanium bromide (2.5 g, 12.65 mmol) was added drop-wise over five minutes and the resulting mixture was stirred for 15 minutes at -95 C. The reaction mixture was warmed to 10 C and quenched with 70 mL of 1M hydrochloric acid, then was extracted with dichloromethane (3 x 25 mL). The aqueous phase was discarded and the combined organic phases were dried over sodium sulfate and concentrated in vacuo to obtain a yellow oil that was combined with the crude product from another reaction and purified by silica gel chromatography (0-5% methanol in dichloromethane) to obtain /V-ie/ -butyl-3-trimethylgermyl- benzenesulfonamide (1.3 g, 64%). ESI-MS m/z calc. 331.0661, found 332.3 (M+l)+; Retention time: 6.2 minutes (LC method C).

Reference： [1]Patent: WO2019/195739,2019,A1 .Location in patent: Paragraph 00231

16
[ 308283-47-8 ]
C₂₃H₂₆ClF₃N₄O₄SSi [ No CAS ]