[ CAS No. 949922-62-7 ] {[proInfo.proName]}

Name: 949922-62-7|tert-Butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate|95%
Brand: Ambeed
SKU: A206027
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Quality Control of [ 949922-62-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 949922-62-7 ]

Product Details of [ 949922-62-7 ]

CAS No. :	949922-62-7	MDL No. :	MFCD09878703
Formula :	C₁₂H₁₆BrNO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ALVKHVFHUNINLV-UHFFFAOYSA-N
M.W :	318.23	Pubchem ID :	19365864
Synonyms :

Calculated chemistry of [ 949922-62-7 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.58
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	77.2
TPSA :	57.78 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) :	-5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.34
Log Po/w (XLOGP3) :	3.38
Log Po/w (WLOGP) :	3.27
Log Po/w (MLOGP) :	2.71
Log Po/w (SILICOS-IT) :	3.74
Consensus Log Po/w :	3.29

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.96
Solubility :	0.0347 mg/ml ; 0.000109 mol/l
Class :	Soluble
Log S (Ali) :	-4.27
Solubility :	0.017 mg/ml ; 0.0000535 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.56
Solubility :	0.0866 mg/ml ; 0.000272 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.96

Safety of [ 949922-62-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 949922-62-7 ]

* 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.

Upstream synthesis route of [ 949922-62-7 ]
Downstream synthetic route of [ 949922-62-7 ]

[ 949922-62-7 ] Synthesis Path-Upstream 1~5

1
[ 230301-73-2 ]
[ 949922-62-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-Bromosuccinimide In acetonitrile at 20℃;	To a solution of 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylic acid tert-butyl ester (5.0 g, 20.89mmol) in acetonitrile (25 mL) N-bromosuccinimide (4.09 g, 22.98 mmol) was stirred at room temperature overnight and the reaction was over, Water (50 mL) was added and extracted with ethyl acetate (50 mL X 2). The organic phases were combined, washed with water (50 mL X 2), saturated brine (40 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography (petroleum ether / ethyl acetate (v/v)=20/1) to give a white solid (6.21 g, 93percent).
92%	With N-Bromosuccinimide In acetonitrile at 20℃; for 1 h;	General procedure: To a solution of thiophenes (10.0 mmol, 1.0 equiv.) in MeCN (10 mL) was added NBS (1.87 g, 1.05 equiv.). After stirred at ambient temperature for 1 h, the reaction mixture was diluted with ethyl acetate (50.0 mL). And the resulting solution was washed with saturated brine and extracted with ethyl acetate (50.0 mL × 2). The combined organic fractions were dried over anhydrous Na₂SO₄, filtered and concentrated under vacuum to yield the crude product. The crude product was chromatographed on silica gel using petroleum ether/ethyl acetate (20:1, v/v) as the eluent to give corresponding products.

Reference： [1] Patent: CN104497008, 2016, B, . Location in patent: Paragraph 0190; 0195; 0196
[2] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 389 - 403

2
[ 230301-73-2 ]
[ 949922-62-7 ]

Reference： [1] Patent: US6015817, 2000, A,

3
[ 24424-99-5 ]
[ 949922-62-7 ]

Reference： [1] Patent: WO2011/110219, 2011, A1, . Location in patent: Page/Page column 15; 1

4
[ 28783-41-7 ]
[ 949922-62-7 ]

Reference： [1] Patent: WO2011/110219, 2011, A1,
[2] Patent: CN104497008, 2016, B,

5
[ 24424-99-5 ]
[ 949922-62-7 ]

Reference： [1] Patent: CN104497008, 2016, B,

[ 949922-62-7 ] Synthesis Path-Downstream 1~52

1
[ 14221-01-3 ]
[ 949922-62-7 ]
[ 98-80-6 ]
[ 1100425-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dimethoxyethane; water;	Step 2 Preparation of N-Boc-2-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine A solution of N-Boc-2-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (Step 1; 637 mg, 0.2 mmol), phenyl boronic acid (244 mg, 0.2 mmol), NaHCO3 (504 mg, 6 mmol) and tetrakis(triphenylphosphine)palladium(O) (116 mg, 0.1 mmol) in DME (10 mL) and water (10 mL) was heated to 80 C. for 20 h. The mixture was partitioned between water and EtOAc, washed with aqueous NaHCO3, water (2*) then brine, dried and evaporated. Column chromatography of the residue (silica gel; hexane/EtOAc 95:5) afforded the title compound as a viscous oil.

Reference： [1]Patent: US6015817,2000,A

2
2-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide [ No CAS ]
[ 230301-73-2 ]
(Boc)2 O [ No CAS ]
[ 949922-62-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In 1,4-dioxane;	Step 1 Preparation of N-Boc-2-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 2-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide (Example 2, Step 2; 6.67 g, 25 mmol) was converted to the Boc-protected derivative using (Boc)2 O (5.46 g, 25 mmol) in 150 mL dioxane and 75 mL 1N NaOH for 2 h. Work-up as described for Example 2, Step 1 afforded the title compound as a solid.

Reference： [1]Patent: US6015817,2000,A

3
[ 28783-41-7 ]
[ 949922-62-7 ]

Reference： [1]Patent: WO2011/110219,2011,A1
[2]Patent: CN104497008,2016,B

4
[ 110-91-8 ]
[ 949922-62-7 ]
[ 1333429-04-1 ]

Yield	Reaction Conditions	Operation in experiment
47%	With potassium phosphate; copper(l) iodide; 2-(N,N-dimethylamino)athanol; copper; at 100℃; for 72h;	General procedure for the synthesis ofADl To a stirredsolution of tert-butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxylate (0.070 g, 0.22 mmol)in 2-(dimethylamino)ethanol (1.0 mL) were added morpholine (0.095 mL, 1.10 mmol), Cul (0.0042 g, 0.022 mmol), Cu (0.0014 g, 0.022 mmol) and Kappa3RhoOmicron4 (0.12 g, 0.55 mmol). The reaction mixture was stiiTed at 100 C for 3 days. After reaction completion, the reaction mixture was diluted with dichloromethane (5 mL) and washed with brine (5 mL). The organic layer was dried over anhydrous MgS04 and concentrated in vacuo. The crude product was purified by flash column chromatography to give AD1 (33.4 mg, yield = 47%).
	With potassium phosphate; copper(l) iodide; copper; In 2-(N,N-dimethylamino)athanol; at 80℃; for 24h;	Example 3 2-(l-morpholinyl) -N-tert.butyloxycarbonyl-4,5,6,7-tetrahydro- thieno[3,2-c]pyridine To a solution of 2-bromo-N-tert.butyloxycarbonyl-4,5,6,7-tetrahydro-thieno[3,2-c] - pyridine (4.24g) in 50 ml Nu,Nu-dimethylethanolamine, copper powder (85 mg), copper iodide (253 mg), potassium phosphate tribasic (7 g) and morpholine (5.8 ml) were added. The reaction mixture was heated to 80C, stirred for 24 hours and left at room temperature for 4 days. Water (100 ml) and dichloromethane (100 ml) were added to the reaction mixture. Separated aqueous layer was extracted once with dichloromethane (100 ml). The organic layers were combined and washed with brine (100 ml). The organic solvent was dried on Na2S04, filtered and evaporated under reduced pressure. Product was purified by column chromatography, (heptane/ethyl acetate 92/8). Yield: 1.23 g, yellow solid

Reference： [1]Patent: WO2015/193506,2015,A1 .Location in patent: Page/Page column 69
[2]Patent: WO2011/110219,2011,A1 .Location in patent: Page/Page column 16

5
2-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine [ No CAS ]
[ 24424-99-5 ]
[ 949922-62-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; for 0.75h;Cooling with ice;	Example 2 2-Bromo-N-tert.butvloxvcarbonvl-4,5,6,7-tetrahvdro-thienor3,2-c1pyridine To a solution of 2-Bromo-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (10 g) in 100 ml dry dichloromethane, triethylamine (12.7 ml) and di-tert-butyldicarbonate (10.8 ml) were added. The reaction mixture was stirred with cooling using an ice bath for 45 minutes. The reaction was followed by HPLC. Reaction mixture was washed with water (100 ml), 1M HC1 (50 ml), sat. NaHCC aq. (50 ml), water (100 ml). Organic solvent was dried on a2S04, filtered and removed solvent under reduced pressure. Crude product was suspended in heptane (15 ml) and diisopropylether (70 ml), and stirred with cooling (ice-bath) for 1 hour. White solid was filtered off and dried overnight at room temperature. Yield: 8.137 g of white solid. Second crop solid was obtained from filtrate, 3.95 g, white solid.

Reference： [1]Patent: WO2011/110219,2011,A1 .Location in patent: Page/Page column 15; 1

6
[ 949922-62-7 ]
[ 150322-43-3 ]

Reference： [1]Patent: WO2011/110219,2011,A1

7
[ 949922-62-7 ]
[ 150322-38-6 ]

Reference： [1]Patent: WO2011/110219,2011,A1

8
[ 949922-62-7 ]
[ 1333429-05-2 ]

Reference： [1]Patent: WO2011/110219,2011,A1

9
[ 949922-62-7 ]
[ 1333429-06-3 ]

Reference： [1]Patent: WO2011/110219,2011,A1

10
[ 949922-62-7 ]
[ 1613148-51-8 ]
[ 1613148-52-9 ]

Yield	Reaction Conditions	Operation in experiment
66%		To a solution of tert-butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxylate (200 mg, 0.63 mmol) and CS2CO3 (409 mg, 1.26 mmol) in dioxane/H20 (6 mL/0.6 mL) was added Pd(dppf)CVCH2Cl2 (51 mg, 0.06 mmol) under a nitrogen atmosphere. The mixture was stirred at 90 C for 30 min, followed by an addition of N,N-bis(?eri- butoxycarbonyl)-3-(l-(5-chloro-2-(trifluoromethyl)phenyl)ethoxy)-5-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)pyridin-2-amine (484 mg, 0.75 mmol). The reaction was heated at 1 10 C overnight, and then concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 12/1) to give the title compound as yellow colloid (314 mg, 66%).
66%		Under nitrogen protection,To a solution of tert-butyl 2-bromo-6,7-dihydrothieno [3,2-c] pyridine-5 (4H) -carboxylate (200 mg, 0.63 mmol) andCesium carbonate (409 mg, 1.26 mmol)Of dioxane / water (6 mL / 0.6 mL)Was added Pd (dppf) Cl2CH2Cl2 (51 mg, 0.06 mmol).After the mixture was stirred at 90 C for 30 minutes,Was added to the system for N, N- bis (tert-butoxycarbonyl) -3- (1- (5-chloro-2- (trifluoromethyl) phenyl) ethoxy) -5- (4,4,5 , 5-tetramethyl-1,3,2-dioxoleBorane-2-yl) pyridin-2-amine (484 mg, 0.75 mmol).The reaction solution was heated to 110 C, stirred overnight and concentrated under reduced pressure.The residue was purified by silica gel column chromatography (PE / EtOAc (v / v) = 12/1)The title compound was obtained as a yellow colloid (314 mg, 66%).

Reference： [1]Patent: WO2014/89324,2014,A1 .Location in patent: Paragraph 0344
[2]Patent: CN104016979,2017,B .Location in patent: Paragraph 1041; 1042

11
[ 949922-62-7 ]
[ 1613148-57-4 ]
[ 1613148-58-5 ]

Yield	Reaction Conditions	Operation in experiment
41%		To a solution of tert-butyl 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)- carboxylate (200 mg, 0.63 mmol) and CS2CO3 (409 mg, 1.26 mmol) in dioxane/H20 (6 mL/0.6 mL) was added Pd(dppf)Ci2-CH2Cl2 (51 mg, 0.06 mmol) under a nitrogen atmosphere. The mixture was heated at 90 C for 30 min, followed by an addition of N,N-bis(/er/- butoxycarbonyl)-3-(l-(2,5-difluorophenyl)ethoxy)-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-2-amine (434 mg, 0.75 mmol). The reaction was heated at 110 C overnight, then cooled to room temperature and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 10/1) to give the title compound as light-yellow colloid (179 mg, 41%). FontWeight="Bold" FontSize="10" H NMR (400 MHz, CDC13) delta (ppm): 8.24 (d, J = 1.6 Hz, 1H), 7.14 -7.10 (m, 2H), 7.08-7.03 (td, J = 8.8 Hz, J = 4.0 Hz, 1H), 6.96-6.90 (m, 2H), 5.71-5.66 (q, J = 6.4 Hz, 1H), 4.47 (s, 2H), 3.72 (s, 2H), 2.84 (s, 2H), 2.04 (s, 2H), 1.65-1.64 (d, J = 6.4 Hz, 3H), 1.48-1.44 (d, J = 15.6 Hz, 27H).
41%		Under nitrogen protection,To a solution of tert-butyl 2-bromo-6,7-dihydrothieno [3,2-c] pyridine-5 (4H) -carboxylate (200 mg, 0.63 mmol)And cesium carbonate (409 mg, 1.26 mmol)Of ethylene glycol dimethyl ether / water (6 mL / 0.6 mL)Was added Pd (dppf) Cl2CH2Cl2 (51 mg, 0.06 mmol).The mixture was heated to 90 C,After stirring for 30 minutes,To a solution of N, N-bis (tert-butoxycarbonyl) -3- (1- (2,5-difluorophenyl) ethoxy) -5- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) pyridin-2-amine (434 mg, 0.75 mmol).The reaction solution was heated to 110 C,Stirred overnight, cooled to room temperature and concentrated under reduced pressure.The residue was purified by silica gel column chromatography (PE / EtOAc (v / v) = 10/1)The title compound was obtained as a pale yellow colloid (179 mg, 41%).

Reference： [1]Patent: WO2014/89324,2014,A1 .Location in patent: Paragraph 0354
[2]Patent: CN104016979,2017,B .Location in patent: Paragraph 1074; 1075; 1076

12
[ 24424-99-5 ]
[ 949922-62-7 ]

Reference： [1]Patent: CN104497008,2016,B

13
[ 230301-73-2 ]
[ 949922-62-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-Bromosuccinimide; In acetonitrile; at 20℃;	To a solution of 6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylic acid tert-butyl ester (5.0 g, 20.89mmol) in acetonitrile (25 mL) N-bromosuccinimide (4.09 g, 22.98 mmol) was stirred at room temperature overnight and the reaction was over, Water (50 mL) was added and extracted with ethyl acetate (50 mL X 2). The organic phases were combined, washed with water (50 mL X 2), saturated brine (40 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography (petroleum ether / ethyl acetate (v/v)=20/1) to give a white solid (6.21 g, 93%).
92%	With N-Bromosuccinimide; In acetonitrile; at 20℃; for 1h;	General procedure: To a solution of thiophenes (10.0 mmol, 1.0 equiv.) in MeCN (10 mL) was added NBS (1.87 g, 1.05 equiv.). After stirred at ambient temperature for 1 h, the reaction mixture was diluted with ethyl acetate (50.0 mL). And the resulting solution was washed with saturated brine and extracted with ethyl acetate (50.0 mL × 2). The combined organic fractions were dried over anhydrous Na2SO4, filtered and concentrated under vacuum to yield the crude product. The crude product was chromatographed on silica gel using petroleum ether/ethyl acetate (20:1, v/v) as the eluent to give corresponding products.

Reference： [1]Patent: CN104497008,2016,B .Location in patent: Paragraph 0190; 0195; 0196
[2]European Journal of Medicinal Chemistry,2018,vol. 145,p. 389 - 403

14
[ 949922-62-7 ]
(S)-2-(5-(aminomethyl)-2-oxooxazolidin-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Patent: CN104497008,2016,B

15
[ 949922-62-7 ]
(S)-2-(5-((5-chlorothiophene-2-carboxamido)methyl)-2-oxooxazolidin-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Patent: CN104497008,2016,B

16
[ 949922-62-7 ]
(S)-5-chloro-N-((2-oxo-3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)oxazolidin-5-yl)methyl)thiophene-2-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: CN104497008,2016,B

17
[ 949922-62-7 ]
(S)-2-(5-((5-chlorothiophene-2-carboxamido)methyl)-2-oxooxazolidin-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide [ No CAS ]

Reference： [1]Patent: CN104497008,2016,B

18
[ 949922-62-7 ]
(S)-N-((3-(5-acetyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)-5-chlorothiophene-2-carboxamide [ No CAS ]

Reference： [1]Patent: CN104497008,2016,B

19
[ 949922-62-7 ]
(S)-2-(5-((5-chlorothiophene-2-carboxamido)methyl)-2-oxooxazolidin-3-yl)-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carboxamide [ No CAS ]

Reference： [1]Patent: CN104497008,2016,B

20
[ 949922-62-7 ]
[ 352524-58-4 ]
(S)-2-(5-((1,3-dioxoisoindolin-2-yl)methyl)-2-oxooxazolidin-3-yl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 110℃;Inert atmosphere;	Under nitrogen, to a sealed tank 50mL sequentially added 2-((5-oxaoxopyrrolidin-3-yl)methyl)isoindoline-1,3-dione (1.85g, 7.5 mmol), <strong>[949922-62-7]2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylic acid tert-butyl ester</strong> (1.59g, 5.0mmol), potassium carbonate (1.38g, 10.0mmol) ,Cuprous iodide (190mg, 1.0mmol), N,N-dimethyl-ethane-1,2-diamine (270muL, 2.50mmol) and 1,4-dioxane (20 mL ), It was stirred and heated to 110 C overnight. After completion of the reaction, water (30mL), (30mL×3) and extracted with ethylacetate. The combined organic phases, according to Washed successively with water (20mL × 2), saturated brine (40 mL),dried over anhydrous sodium sulfate. Filter, evaporate the solvent, the crude product was purified by column Chromatography(petroleum ether/ethyl acetate (v/v) = 2/1), give an off-white solid (1.85g, 76%).

Reference： [1]Patent: CN104497008,2016,B .Location in patent: Paragraph 0190; 0198; 0199

21
[ 949922-62-7 ]
[ 68-12-2 ]
[ 165947-55-7 ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: To a solution of heteroarylenes or bromo-heteroarylenes (3.75 mmol, 1.0 equiv.) in dry THF (30.0 mL) was added n-BuLi (2.5 M in THF; 1.8 mL) dropwise at -78 C under an argon atmosphere. The reaction mixture was stirred for 1 h (5 min for 86) at -78 C. To the mixture was added the dry DMF (330 mg, 4.51 mmol). After stirred for additional 1 h, the reaction solution was quenched with 1.0 mL H2O. And the resulting solution was washed with saturated brine and extracted with ethyl acetate (50.0 mL × 3). The combined organic fractions were dried over anhydrous Na2SO4, filtered and concentrated under vacuum to yield the crude product. The crude product was chromatographed on silica gel using petroleum ether/ethyl acetate (10:1, v/v) as the eluent to give corresponding products.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 145,p. 389 - 403

22
[ 949922-62-7 ]
C₃₅H₃₅FO₆ [ No CAS ]
C₄₇H₅₂FNO₈S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3446 - 3453

23
[ 949922-62-7 ]
4-(benzyloxy)-5-((3R,4R,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5-fluoro-2-hydroxytetrahydro-2H-pyran-2-yl)-2-methylbenzaldehyde [ No CAS ]
tert-butyl 2-((4-(benzyloxy)-5-((3R,4R,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5-fluoro-2-hydroxytetrahydro-2H-pyran-2-yl)-2-methylphenyl)(hydroxy)methyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of <strong>[949922-62-7]tert-butyl 2-bromo-4H,5H,6H,7H-thieno[3,2-c]pyridine-5-carboxylate</strong> (1.62 g, 5.09 mmol, 3.00 equiv) in tetrahydrofuran (16 mL) was added n-BuLi (2.5M in hexane, 2.03 mL, 5.09 mmol, 3.00 equiv) dropwise at -78 C., and the mixture was stirred for 25 mins at -78 C. 4-(Benzyloxy)-5-((3R,4R,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5-fluoro-2-hydroxytetrahydro-2H-pyran-2-yl)-2-methylbenzaldehyde (1.15 g, 1.70 mmol, 1.00 equiv) in tetrahydrofuran (4 mL) was then added to the solution. The reaction was stirred for 2 h at -78 C. NH4Cl/H2O was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2SO4. The mixture was then concentrated and purified by chromatography on silica gel (3:1 PE/EA) to yield tert-butyl 2-((4-(benzyloxy)-5-((3R,4R,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5-fluoro-2-hydroxytetrahydro-2H-pyran-2-yl)-2-methylphenyl)(hydroxy)methyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate as a yellow oil.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3446 - 3453
[2]Patent: US2019/55226,2019,A1 .Location in patent: Paragraph 0448

24
[ 949922-62-7 ]
2-(5-((2S,3S,4R,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5-fluorotetrahydro-2H-pyran-2-yl)-2-methylbenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

25
[ 949922-62-7 ]
2-(5-((2S,3S,4R,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5-fluorotetrahydro-2H-pyran-2-yl)-2-methylbenzyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carbonitrile [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

26
[ 949922-62-7 ]
2-(5-((2S,3R,4R,5S,6R)-5-fluoro-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-2-methylbenzyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carbonitrile [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

27
[ 949922-62-7 ]
tert-butyl 2-(5-bromo-2-methylbenzyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

28
[ 949922-62-7 ]
tert-butyl 2-(5-((3R,4R,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5-fluoro-2-hydroxytetrahydro-2H-pyran-2-yl)-2-methylbenzyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

29
[ 949922-62-7 ]
(2-(5-((2S,3S,4R,5R,6R)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)-5-fluorotetrahydro-2H-pyran-2-yl)-2-methylbenzyl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)(thiazol-2-yl)methanone [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

30
[ 949922-62-7 ]
(2-(5-((2S,3R,4R,5S,6R)-5-fluoro-3,4-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yl)-2-methylbenzyl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)(thiazol-2-yl)methanone [ No CAS ]

Reference： [1]Patent: US2019/55226,2019,A1

31
[ 949922-62-7 ]
[ 90050-59-2 ]
tert-butyl 2-((5-bromo-2-methylphenyl)(hydroxy)methyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate [ No CAS ]