263351-43-5|tert-Butyl 3-iodobenzylcarbamate| Ambeed

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Quality Control of [ 263351-43-5 ] Purity: 95% SDS Specification

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Product Details of [ 263351-43-5 ]

CAS No. :	263351-43-5
Formula :	C₁₂H₁₆INO₂
M.W :	333.17
SMILES Code :	O=C(OC(C)(C)C)NCC1=CC=CC(I)=C1
MDL No. :	MFCD09032539
InChI Key :	JWXVKTCSHBWQRQ-UHFFFAOYSA-N
Pubchem ID :	11645663

Safety of [ 263351-43-5 ]

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

Application In Synthesis of [ 263351-43-5 ]

* 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 [ 263351-43-5 ]

[ 263351-43-5 ] Synthesis Path-Downstream 1~33

1
[ 57-63-6 ]
[ 263351-43-5 ]
[3-(3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ylethynyl)-benzyl]-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 839 - 842.

2
[ 878270-28-1 ]
[ 263351-43-5 ]
2-benzyloxycarbonylamino-3-{3-[3-(tert-butoxycarbonylamino-methyl)-phenyl]-prop-2-ynyloxy}-propionic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 1817 - 1824.

3
[ 263351-43-5 ]
(8R,9S,13S,14S,17S)-17-(3-Aminomethyl-phenylethynyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol [ No CAS ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 839 - 842.

4
[ 24424-99-5 ]
[ 3718-88-5 ]
[ 263351-43-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; at 20℃; for 1.5h;	A suspension of 3-iodobenzylamine hydrochloride (4.95 g, 18.4 mrnol) in dichloromethane (100 mL) was treated with trieihylamine (3.1 mL, 22 mmol) and di-tert-butyl dicarbonate (4.40 g, 20 mmol) artid the resulting solution stirred at room temperature for 1.5 hours. The reaction fixture was then washed with 2M hydrochloric acid (30 mL), water (30 mL), cried over sodium sulfate and concentrated in vacuo to afford the title compound as a colourless solid in quantitative yield, 6.43 g. HNMR (400MHz, CDCI3) 8 : 1.46 (9H, s), 4.21-4. SO (2H, m), 4. 79-4. 89 (1 H, bs), 7.06 (1H, dd), 7.25 (1H, d), 7.60 (1H, d), 7.63 (1H, s); LRMS ESl m/z 332 [M-H]-
	With triethylamine; In dichloromethane; at 20℃; for 1.5h;	A suspension of 3-iodobenzylamine hydrochloride (4.95g, 18.4 mmol) in dichloromethane (100 ml) was treated with triethylamine (3.1 ml, 22 mmol) and di-t-butyl dicarbonate (4.40g, 20 mmol) and the resulting solution left to stir at room temperature under a nitrogen atmosphere for 1.5 hours. The reaction mixture was washed with 2M hydrochloric acid (30 ml), water (30 ml), dried (sodium sulfate), and the solvent removed in vacuo to give the title compound as a colourless solid (6.43g). 1HNMR (400 MHz, CDCl3) delta: 1.46 (s, 9H), 4.21-4.30 (m, 2H), 4.79-4.89 (bs, 1H), 7.06 (dd, 1H), 7.25 (d, 1H), 7.60 (d, 1H), 7.63 (s, 1H) ppm. MS (electrospray) m/z 332 [M-H]-, 356 [M+Na]+
	With triethylamine; In dichloromethane; at 20℃; for 1.5h;	A suspension of 3-iodobenzylamine hydrochloride (4.95 g, 18.4 mmol) in dichloromethane (100 ml) was treated with triethylamine (3.1 ml, 22 mmol) and di-t-butyl dicarbonate (4.40 g, 20 mmol) and the resulting solution left to stir at room temperature under a nitrogen atmosphere for 1.5 hours. The reaction mixture was washed with 2M hydrochloric acid (30 ml), water (30 ml), dried (sodium sulfate), and the solvent removed in vacuo to give the title compound as a colourless solid (6.43 g). 1HNMR (400 MHz, CDCl3) delta: 1.46 (s, 9H), 4.21-4.30 (m, 2H), 4.79-4.89 (bs, 1H), 7.06 (dd, 1H), 7.25 (d, 1H), 7.60 (d, 1H), 7.63 (s, 1H) ppm. MS (electrospray) m/z 332 [M-H]-, 356 [M+Na]+

	With triethylamine; In dichloromethane; at 20℃; for 1h;	Example 150: Synthesis of 4-Chloro-6-[3-(3-dimethylamino-propylamino)- benzylamino]-2//-phthalazin-l-one hydroformate; (3-Iodo-benzyl)-carbamic acid tert-butyl ester; A mixture of 3-iodobenzylamine hydrochloride (3g, 11.131 mmol), CH2Cl2(6OmL) and triethylamine (3.ImL, 22.263 mmol) was stirred at room temperature. Boc- anhydride (2.6Og, 11.913 mmol) was added and the reaction stirred at room temperature for Ih. The reaction was poured onto water, extracted with CH2Cl2 and dried (Na2SO4). Preparatory HPLC afforded (3-iodo-benzyl)-carbamic acid tert-butyl ester (3.494g) as a white solid, m/z (M+l) 333.84.
	With triethylamine; In dichloromethane; at 20℃; for 1.5h;	A suspension of 3-iodobenzylamine hydrochloride (4.95g, 18.4mmol) in dichloromethane (100ml) was treated with triethylamine (3.1ml, 22mmol) and di-t-butyl dicarbonate (4.40g, 20mmol) and the resulting solution left to stir at room temperature under a nitrogen atmosphere for 1.5 hours. The reaction mixture was washed with 2M hydrochloric acid (30ml), water (30ml), dried (sodium sulfate), and the solvent removed in vacua to give the title compound as a colourless solid (6.43g).1HNMR (400MHz, CDCI3) 5 :7.63 (s, 1H), 7.60 (d, 1H), 7.25 (d, 1H), 7.06 (dd, 1H), 4.79-4.89 (bs, 1H), 4.21-4.30 (m, 2H), 1.46 (s, 9H) ppm.MS (electrospray) m/z 332 [M-H]', 356 [M+Na]"1"

References: [1]Patent: WO2005/92840,2005,A1 .Location in patent: Page/Page column 73.
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1488 - 1492.
[3]Patent: US2005/182091,2005,A1 .Location in patent: Page/Page column 31-32.
[4]Patent: US2005/222128,2005,A1 .Location in patent: Page/Page column 47.
[5]Patent: WO2008/61108,2008,A2 .Location in patent: Page/Page column 115.
[6]Patent: WO2004/108676,2004,A1 .Location in patent: Page 161.

5
[ 71597-85-8 ]
[ 263351-43-5 ]
[ 808769-21-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 16h;	A solution of the product of preparation 49 (0.75 g, 2.25 mmol), 4-hydroxy phenylboronic acid (0.62 g, 4.50 mmol) and 1, 1'- bis (diphenylphosphino) ferrocenyl palladium (II) chloride (0.11 g, 0.14 mrnol) in N, N-dimethylformamide (14 mL) was treated with 2M aqueous sodium carbonate solution (4 mL) and the resulting mixture was heated at 80 C for 16 hours. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel, eluting with ethyl acetate: pentane, 25: 75, to afford the title compound as a pale pink crystalline solid in quantitative yield, 0. 73 g. 'H NMR (400MHz, CDCI3) 8 : 1.47 (9H, s), 4. 33-4. 41 (2H, m), 4. 87-4. 94 (1H, bs), 6.89 (2H, d), 7.21 (1H, d), 7.37 (1H, dd), 7.43-7. 45 (4H, m); LRMS ESI m/z 298 [M-H]-
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 16h;	A solution of the iodide from preparation 61 (0.75g, 2.25 mmol), 4-hydroxy phenylboronic acid (0.62g, 4.50 mmol), 1,1'-bis(diphenylphosphino)ferrocenyl palladium(II)chloride (0.11g, 0.14 mmol), in N,N-dimethylformamide (14 ml) was treated with 2M aqueous sodium carbonate (4 ml) and the resulting mixture heated at 80 C. under a nitrogen atmosphere for 16 hours. The solvent was removed in vacuo and the residue purified by column chromatography on silica gel eluting with ethyl acetate:pentane (1:3) to give the title compound as a pale pink crystalline solid (0.73g). 1HNMR (400 MHz, CDCl3) delta: 1.47 (s, 9H), 4.33-4.41 (m, 2H), 4.87-4.94 (bs, 1H), 6.89 (d, 2H), 7.21 (d, 1H), 7.37 (dd, 1H), 7.43-7.45 (m, 4H) ppm. MS (electrospray) m/z 298 [M-H]-, 322 [M+Na]+
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 16h;	A solution of the iodide from preparation 131 (0.75 g, 2.25 mmol), 4-hydroxy phenylboronic acid (0.62 g, 4.50 mmol), 1,1'-Bis(diphenylphosphino)ferrocenyl palladium(II)chloride (0.11 g, 0.14 mmol), in N,N-dimethylformamide (14 ml) was treated with 2M aq. sodium carbonate (4 ml) and the resulting mixture heated at 80 C. under a nitrogen atmosphere for 16 hours. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with ethyl acetate:pentane (1:3) to give the title compound as a pale pink crystalline solid (0.73 g). 1HNMR (400 MHz, CDCl3) delta: 1.47 (s, 9H), 4.33-4.41 (m), 4.87-4.94 (bs, 1H), 6.89 (d, 2H), 7.21 (d, 1H), 7.37 (dd, 1H), 7.43-7.45 (m, 4H) ppm. MS (electrospray) m/z 298 [M-H]-, 322 [M+Na]+

With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 16h;

A solution of the iodide from preparation 75 (0.75g, 2.25mmol), 4-hydroxy phenylboronic acid (0.62g, 4.50mmol), 1,1'-bis(diphenylphosphino)ferrocenyl palladium(ll)chloride (0.11g, 0.14mmol), in A/,A/-dimethylformamide (14ml) wastreated with 2M aq. sodium carbonate (4ml) and the resulting mixture heated at 80C under a nitrogen atmosphere for 16 hours. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with ethyl acetate:pentane (1:3) to give the title compound as a pale pink crystalline solid ( 0.73g).1HNMR (400MHz, CDCI3) 5 : 7.43-7.45 (m, 4H), 7.37 (dd, 1H), 7.21 (d, 1H), 6.89 (d, 2H), 4.87-4.94 (bs, 1H), 4.33-4.41 (m, 2H), 1.47 (s, 9H) ppm.MS (electrospray) m/z 298 [M-H]", 322 [M+Naf

References: [1]Patent: WO2005/92840,2005,A1 .Location in patent: Page/Page column 73.
[2]Patent: US2005/182091,2005,A1 .Location in patent: Page/Page column 32.
[3]Patent: US2005/222128,2005,A1 .Location in patent: Page/Page column 47.
[4]Patent: WO2004/108676,2004,A1 .Location in patent: Page 160-161.

6
[ 24424-99-5 ]
[ 696-40-2 ]
[ 263351-43-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With triethylamine; In dichloromethane; at 20℃; for 4.5h;	In a 100 rnL round-bottom flask with magnetic stirrer and balloon (for pressure equalization and exclusion of moisture), a solution of di-tert-buty dicarbonate (0.72 g, 3.3 mmol, 1.2 equiv.) in CH2Cl2 (5 mL) was added all at once at room temperature to a solution of 3-iodobenzylamine (641 mg, 2.75 mmol) and triethylamine (0.57 mL, 4.1 mmol, 1.5 equiv.) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 4.5 h. TLC after 3.5 h (SiO2, EtOAc/hexane/Et3N 22:78:5) indicated complete conversion of the amine (Rf approx. 0.05), whereas a strongly UV-active impurity (R{ approx. 0.65) remained unchanged, and the product was detected at R{ approx. 0.55. With EtOAc/hexane 1:9 as eluent, product and impurity exhibit R{ values of approx. 0.2 and 0.4, respectively. The reaction mixture was evaporated, and the residue was chromato graphed on SiO2 (26 x 3.8 cm, EtOAc/hexane 6:94 until the nonpolar impurity was completely eluted, then 1:4). Evaporation and drying (40 C/oil pump) furnished 820 mg (89%) of a colorless solid. Mp 53.5-54.5 0C. MS (EI) m/z 333 (M+, 0.2%), 277 (33%), 276 (38%), 232 (6.4%), 217 (11%), 150 (5.4%), 106 (19%), 59 (26%), 57 (100%).
88%	In dichloromethane; at 20℃; for 12h;	To a stirred solution containing 1 mL (7.5 MMOL) of 3-iodobenzylamine and 15 mL of DICHLOROMETHANE was added 1.7 g (7.87 MMOL) of di-tert-butyl dicarbonate. The reaction mixture was allowed to stir at room temperature for 12 h, then diluted with ether and washed successively with water, 10% aqueous NAOH, 10% aqueous HCI, and brine, and dried over MGS04. The solvents were removed under reduced pressure to give the title compound as a white solid (2.20g, 88%). 1H NMR (300 MHz, CDCI3) 95 1. 45 (s, 9H), 4.26 (d, 2H, J = 6.0 Hz), 4.83 (brs, 1H), 7.05 (dd, 1H, J = 7.5 and 7.5 Hz), 7.24 (d, 1H, J = 7.5 Hz), 7.58 (d, 1 H, J = 7.5 Hz), and 7.62 (s, 1 H).
	With triethylamine; In dichloromethane; at 20℃; for 4.5h;	Example 25 tert-Butyl [3-[5-[(2(S)-Azetidinyl)methoxy]-3-pyridyl]benzyl]carbamate RRN 394 tert-Butyl 3-Iodobenzylcarbamate [1332] di-tert-butyl dicarbonate (0.72 g, 3.3 mmol, 1.2 equiv.) in CH2Cl2 (5 mL) was added all at once at room temperature to a solution of 3-iodobenzylamine (641 mg, 2.75 mmol) and triethylamine (0.57 mL, 4.1 mmol, 1.5 equiv.) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 4.5 h. TLC after 3.5 h (SiO2, EtOAc/hexane/Et3N 22:78:5) indicated complete conversion of the amine (Rf approx. 0.05), whereas a strongly UV-active impurity (Rf approx. 0.65) remained unchanged, and the product was detected at Rf approx. 0.55. With EtOAc/hexane 1:9 as eluent, product and impurity exhibit Rf values of approx. 0.2 and 0.4, respectively. The reaction mixture was evaporated, and the residue was chromatographed on SiO2 (26×3.8 cm, EtOAc/ hexane 6:94 until the nonpolar impurity was completely eluted, then 1:4). Evaporation and drying (40 C./oil pump) furnished 820 mg (89%) of a colorless solid. Mp 53.5-54.5 C. MS (EI) m/z 333 (M+, 0.2%), 277 (33%), 276 (38%), 232 (6.4%), 217 (11%), 150 (5.4%), 106 (19%), 59 (26%), 57 (100%).

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9122 - 9135.
[2]Patent: WO2010/45212,2010,A2 .Location in patent: Page/Page column 241.
[3]Patent: WO2005/16914,2005,A1 .Location in patent: Page/Page column 74.
[4]Patent: US2013/184313,2013,A1 .Location in patent: Paragraph 1332; 1333.

7
[ 4039-82-1 ]
[ 263351-43-5 ]
C₂₂H₂₅NO₃ [ No CAS ]

References: [1]Patent: US2005/256145,2005,A1 .Location in patent: Page/Page column 37.

8
[ 109-55-7 ]
[ 263351-43-5 ]
[ 1028338-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 80℃; for 1.5h;	[3-(3-dimethylamino-propylamino)-benzyl]-carbamic acid tert-butyl ester; A mixture of <strong>[263351-43-5](3-iodo-benzyl)-carbamic acid tert-butyl ester</strong> (150mg, 0.450mmol), 3 -(dimethylamino)-l -propylamine (0.084mL, 0.675mmol), K2CO3 (129mg, 0.933 mmol), CuI (1 lmg, 0.058 mmol), L-proline (13mg, 0.113mmol) and DMSO (3 mL) was heated at 8O0C for 1.5h. The reaction was cooled, poured onto water and the aqueous layer extracted with EtOAc (x3). The organic layers were combined and washed with water, <n="117"/>brine and dried (Na2SO4). Chromatography (MeOH/EtOAc) afforded [3-(3-dimethyl amino-propylamino)-benzyl]-carbamic acid tert-buty ester (65mg) as a yellow solid, m/z (M+l) 308.13.

References: [1]Patent: WO2008/61108,2008,A2 .Location in patent: Page/Page column 115-116.

9
[ 2038-03-1 ]
[ 263351-43-5 ]
[ 1028338-70-6 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 80℃; for 1h;	Example 151: Synthesis of 4-Chloro-6-[3-(2-morpholin-4-yl-ethylamino)- benzylamino]-2H-phthalazin-l -one hydroformate; [3-(2-Morpholin-4-yl-ethylamino)-benzyl]-carbamic acid isopropyl ester; A mixture of <strong>[263351-43-5](3-iodo-benzyl)-carbamic acid tert-butyl ester</strong> (272mg, 0.816mmol),4-(2-aminoethyl)morpholine (O.lbetamL, 1.225 mmol), K2CO3 (232mg, 1.679 mmol), CuI <n="118"/>(19mg, 0.10 mmol), L-proline (19mg, 0.163mmol) and DMSO (5 mL) was heated at 85C for Ih. The reaction was cooled, poured onto water and the aqueous layer extracted with EtOAc (x3). The organic layers were combined and washed with water, brine and dried (Na2SO4). Chromatography (MeOH/EtOAc) afforded [3-(2-morpholin-4-yl- ethylamino)-benzyl]-carbamic acid isopropyl ester (200mg) as an orange viscous oil. m/z (M+l) 336.16.

References: [1]Patent: WO2008/61108,2008,A2 .Location in patent: Page/Page column 116-117.

10
N-({(5S)-3-[3-Fluoro-4-(4-hex-5-ynoylpiperazin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide [ No CAS ]
[ 263351-43-5 ]
[ 773128-15-7 ]

Yield	Reaction Conditions	Operation in experiment
		tert-Butyl 3-iodobenzylcarbamate (0.67 mmol) was dissolved in 1 mL of dry DMF and the resultant solution was evacuated to 40 mm pressure and then released to N2 (g) three times. Triethylamine (1:8 ratio with DMF, 100 muL), Pd(PPh3)2Cl2 (0.030 mmol), and CuI (0.067 mmol) were added. The resultant mixture evacuated to 40 mm pressure for Ca. 30 seconds and then released to N2 (g). Finally, the alkyne 4 (0.67 mmol) in DMF (0.07 M) was added dropwise via an addition funnel over 40 minutes. The reaction mixture was stirred at room temperature for 18 hr and then diluted with ethyl acetate, poured into 0.1 M HCl and extracted with EtOAc (3×100 mL). The combined organic layers were washed with water and brine and dried over MgSO4. The extract was concentrated and the product purified by Biotage chromatography (40M, product loaded onto SiO2) with 2% MeOH/CH2Cl2 to afford the desired title compound: 1H NMR (400 MHz, DMSO-d6) delta 8.24 (m, 1H), 7.50 (dd, J=4, 16 Hz, 1 H), 7.41 (m, 1H), 7.26 (m, 3H), 7.18 (m, 2H), 7.05 (m, 1H), 4.71 (m, 1H), 4.08 (m, 3H), 3.70 (dd, J=4, 12 Hz, 1H), 3.62 (m, 4H), 3.40 (m, 2H), 2.92 (m, 4H), 2.47 (m, 4H), 1.83 (s, 3H), 1.79 (m, 2H), 1.38 (s, 9H).

References: [1]Patent: US2004/204463,2004,A1 .Location in patent: Page 6.

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine; In dichloromethane; at 20℃;	General procedure: To a stirred solution of benzylamine derivative (1 equiv.) in dry DCM, triethylamine (1 .5 equiv.) and di-tert-butyl dicarbonate (1 -1 .2 equiv.) were added under azote atmosphere. The reaction mixture was stirred at room temperature until completion. Water was then added, the phases were separated and the aqueous phase was extracted once with DCM. The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated under vacuum. The crude mixture was then purified by flash column chromatography (0-10% MeOH in DCM) to provide the expected compound. The following compounds are examples illustrating this procedure:; tert-butyl bomophenyl)methyllcarbamate was prepared from 3- bromobenzylamine (2 g, 10.75 mmol). Yield: 2.47g (80%) of the title compound as a white powder

12
[ 704914-05-6 ]
[ 263351-43-5 ]
[ 1222138-84-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In N,N-dimethyl-formamide; at 50℃; for 6h;	3-[[l-(Benzyloxycarbonyl)-2(S)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine (682 mg, 1.48 mmol), <strong>[263351-43-5]tert-butyl 3-iodobenzylcarbamate</strong> (498 mg, 1.48 mmol), and anhydrous DMF (5 mL) were placed in a 50 mL round-bottom flask with magnetic stirrer. To this mixture were added rapidly CsF (450 mg, 2.96 mmol, 2 equiv.), CuI (29 mg, 0.15 mmol, 0.1 equiv.), and tetrakis(triphenylphosphine)palladium(0) (87 mg, 75 mumol, 0.05 equiv.). The flask was fitted with a three-way stopcock with argon balloon, and the atmosphere was exchanged. The reaction mixture was heated at 50 0C for 6 h, during which time it turned from an olive-colored solution to a dark suspension. The solvent was pumped off at 30 0C with an oil pump into a -78 0C receiver. The residue was stirred with ether (20 mL) to disperse the solid, which was then removed by suction filtration over celite. The filter residue was twice washed with ether (15 mL each), and the combined ether solutions were evaporated. TLC (SiO2, EtOAc) showed the formation of a major product at Rf 0.5 (UV-and KMnO4-active) followed by residual DMF (Rf 0.15; KMnO4 stain only). The crude product was chromato graphed on silica gel (20 x 3.8 cm) with a stepwise gradient of EtOAc/hexane 1:1, 2:1, 3:1, and 4:1. The product-containing eluate fractions were evaporated. The residue was taken up in DMSO (2.2 mL) and further purified by preparative HPLC in a single portion on a Supelco Discovery C1S column (250 x 21.2 mm, 5 mum particle size; UV detection at 270 nm; flow/solvent gradient: 0-12 min, 6 to 12.5 niL/min (then remaining at this value)/20% CH3CN in water; 20-100% within 40 min; run aborted after elution of the main peak and column washed with CH3CN). The product eluted at fo 39.8- 41.9 min. Evaporation and drying (50 C/oil pump) gave 542 mg (73%) of a yellowish glass. [alpha]D -44.3, [(X]546 -52.5 (c 10.5 g/L, EtOAc). 1H NMR (CDCl3, 500 MHz) delta 8.48 (s, IH), 8.32 (br, IH), 7.51-7.25 (m, 10H), 5.13, 5.09 (ABq, 2H, J = 12.4 Hz), 4.96 (br, IH), 4.67 (br, IH), approx. 4.5 (very br, IH), 4.42 (br d, 2H, J = 5.3 Hz), 4.22 (br, IH), 4.08-4.00 (m, 2H), 2.51- 2.32 (m, 2H), 1.50 (s, 9H). MS (EI) m/z 503 (M+, 0.6%), 447 (1.5%), 312 (2.4%), 199 (2.6%), 91 (100%), 57 (18%).
73%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In N,N-dimethyl-formamide; at 50℃; for 6h;Inert atmosphere;	tert-Butyl [3-[5-[[1-(Benzyloxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]benzyl]carbamate 3-[[1-(Benzyloxycarbonyl)-2(S)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine (682 mg, 1.48 mmol), <strong>[263351-43-5]tert-butyl 3-iodobenzylcarbamate</strong> (498 mg, 1.48 mmol), and anhydrous DMF (5 mL) were placed in a 50 mL round-bottom flask with magnetic stirrer. To this mixture were added rapidly CsF (450 mg, 2.96 mmol, 2 equiv.), CuI (29 mg, 0.15 mmol, 0.1 equiv.), and tetrakis(triphenylphosphine)palladium(0) (87 mg, 75 mumol, 0.05 equiv.). The flask was fitted with a three-way stopcock with argon balloon, and the atmosphere was exchanged. The reaction mixture was heated at 50 C. for 6 h, during which time it turned from an olive-colored solution to a dark suspension. The solvent was pumped off at 30 C. with an oil pump into a -78 C. receiver. The residue was stirred with ether (20 mL) to disperse the solid, which was then removed by suction filtration over celite. The filter residue was twice washed with ether (15 mL each), and the combined ether solutions were evaporated. TLC (SiO2, EtOAc) showed the formation of a major product at Rf 0.5 (UV- and KMnO4-active) followed by residual DMF (Rf 0.15; KMnO4 stain only). The crude product was chromatographed on silica gel (203.8 cm) with a stepwise gradient of EtOAc/hexane 1:1, 2:1, 3:1, and 4:1. The product-containing eluate fractions were evaporated. The residue was taken up in DMSO (2.2 mL) and further purified by preparative HPLC in a single portion on a Supelco Discovery C18 column (25021.2 mm, 5 mum particle size; UV detection at 270 nm; flow/solvent gradient: 0-12 min, 6 to 12.5 mL/min (then remaining at this value)/20% CH3CN in water; 20-100% within 40 min; run aborted after elution of the main peak and column washed with CH3CN). The product eluted at tR 39.8-41.9 min. Evaporation and drying (50 C./oil pump) gave 542 mg (73%) of a yellowish glass. [alpha]D -44.3, [alpha]546 -52.5 (c 10.5 g/L, EtOAc). 1H NMR (CDCl3, 500 MHz) delta 8.48 (s, 1H), 8.32 (br, 1H), 7.51-7.25 (m, 10H), 5.13, 5.09 (ABq, 2H, J=12.4 Hz), 4.96 (br, 1H), 4.67 (br, 1H), approx. 4.5 (very br, 1H), 4.42 (br d, 2H, J=5.3 Hz), 4.22 (br, 1H), 4.08-4.00 (m, 2H), 2.51-2.32 (m, 2H), 1.50 (s, 9H). MS (EI) m/z 503 (M+, 0.6%), 447 (1.5%), 312 (2.4%), 199 (2.6%), 91 (100%), 57 (18%).

References: [1]Patent: WO2010/45212,2010,A2 .Location in patent: Page/Page column 241-242.
[2]Patent: US2013/184313,2013,A1 .Location in patent: Paragraph 1334; 1335.

13
[ 1228693-09-1 ]
[ 263351-43-5 ]

References: [1]Chemistry - A European Journal,2010,vol. 16,p. 4557 - 4566.

14
[ 873-73-4 ]
[ 263351-43-5 ]
C₂₀H₂₀ClNO₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1488 - 1492.

15
[ 263351-43-5 ]
[ 1283596-43-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1488 - 1492.

16
[ 263351-43-5 ]
[ 1283596-51-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1488 - 1492.

17
[ 263351-43-5 ]
C₂₂H₁₇ClIN [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1488 - 1492.

18
[ 263351-43-5 ]
[ 1309877-90-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1488 - 1492.

19
[ 263351-43-5 ]
N-(3-(5-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridin-3-yl)benzyl)acetamide [ No CAS ]