[ CAS No. 124931-12-0 ]

Name: 124931-12-0|Diethyl (2-(methoxy(methyl)amino)-2-oxoethyl)phosphonate|98%
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Product Details of [ 124931-12-0 ]

CAS No. :	124931-12-0	MDL No. :	MFCD00134233
Formula :	C₈H₁₈NO₅P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	239.21 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 124931-12-0 ]

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

Application In Synthesis of [ 124931-12-0 ]

* 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 [ 124931-12-0 ]

[ 124931-12-0 ] Synthesis Path-Downstream 1~32

1
[ 26489-02-1 ]
[ 124931-12-0 ]
[ 141868-91-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydride In diethyl ether for 1h; 0 deg C to room temperature;
50%	With sodium hydride In tetrahydrofuran at -78 - 20℃; for 17h; Inert atmosphere;

Reference： [1]Netz, David F.; Seidel, Jimmy L. [Tetrahedron Letters, 1992, vol. 33, # 15, p. 1957 - 1958]
[2]Drissi-Amraoui, Sammy; Morin, Marie S. T.; Crévisy, Christophe; Baslé, Olivier; Marciadefigueiredo, Renata; Mauduit, Marc; Campagne, Jean-Marc [Angewandte Chemie - International Edition, 2015, vol. 54, # 40, p. 11830 - 11834][Angew. Chem., 2015, vol. 127, # 40, p. 11996 - 12000,5]

2
[ 124931-12-0 ]
[ 432-25-7 ]
[ 141208-06-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With n-butyllithium In tetrahydrofuran; hexane for 24h; Ambient temperature;
	With sodium hydride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
1.43 g	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;

Reference： [1]Groesbeek, M.; Rood, G. A.; Lugtenburg, J. [Recueil des Travaux Chimiques des Pays-Bas, 1992, vol. 111, # 3, p. 149 - 154]
[2]Drissi-Amraoui, Sammy; Morin, Marie S. T.; Crévisy, Christophe; Baslé, Olivier; Marciadefigueiredo, Renata; Mauduit, Marc; Campagne, Jean-Marc [Angewandte Chemie - International Edition, 2015, vol. 54, # 40, p. 11830 - 11834][Angew. Chem., 2015, vol. 127, # 40, p. 11996 - 12000,5]
[3]Livingstone, Keith; Tenberge, Marius; Pape, Felix; Daniliuc, Constantin G.; Jamieson, Craig; Gilmour, Ryan [Organic Letters, 2019, vol. 21, # 23, p. 9677 - 9680]

3
[ 124931-12-0 ]
[ 150943-17-2 ]
[ 153474-56-7 ]
[ 150943-18-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 4.6%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: (2R)-1-(tert-butyloxycarbonyl)-2-((tert-butyldiphenylsilyl)oxymethyl)-3-azetidinone In tetrahydrofuran at 20℃; for 14h;
1: 67% 2: 7.7%	In methanol at -78 - 20℃; for 25h;
	With sodium hydride In tetrahydrofuran at 0℃; Yield given. Yields of byproduct given;

Reference： [1]Hanessian, Stephen; Fu, Jian-Min [Canadian Journal of Chemistry, 2001, vol. 79, # 11, p. 1812 - 1826]
[2]Hanessian, Stephen; Fu, Jian-Min [Canadian Journal of Chemistry, 2001, vol. 79, # 11, p. 1812 - 1826]
[3]Hanessian, Stephen; Fu, Jian-Min; Chiara, Jose-Luis; Fabio, Romano Di [Tetrahedron Letters, 1993, vol. 34, # 26, p. 4157 - 4160]

4
[ 124931-12-0 ]
[ 108-94-1 ]
[ 124931-20-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydride In diethyl ether for 1h; 0 deg C to room temperature;
	With n-butyllithium 1.) THF, -78 deg C, 2.) 0 deg C, 1 h; Yield given. Multistep reaction;

Reference： [1]Netz, David F.; Seidel, Jimmy L. [Tetrahedron Letters, 1992, vol. 33, # 15, p. 1957 - 1958]
[2]Nuzillard, Jean-Marc; Boumendjel, Ahcene; Massiot, Georges [Tetrahedron Letters, 1989, vol. 30, # 29, p. 3779 - 3780]

5
[ 124931-12-0 ]
[ 100-52-7 ]
N-methoxy-N-methylcinnamamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: benzaldehyde In tetrahydrofuran at -78 - 20℃;	HWE Reaction; General Procedure A General procedure: Diethyl 2-[methoxy(methyl)amino]-2-oxoethylphosphonate (1; 1.2 equiv) was dissolved in anhyd THF and NaH (1.2 equiv) was added portionwise at r.t. until gas evolution ceased. The mixture was then cooled to -78 °C and the appropriate benzaldehyde derivative (1 equiv) dissolved in anhyd THF was added. The reaction mixture was stirred at -78 °C for 1 h, then allowed to warm to r.t. and stirred overnight. H2O (10 mL) was added, the layers were separated, and the organic layer was washed with sat. aq NaHCO3 (2 × 10 mL). The combined aqueous phases were extracted with EtOAc (3 × 15 mL). The combined organic phases were then washed with brine (2 × 10 mL) ,dried (MgSO4), and concentrated in vacuo. If necessary, the crude product was purified by flash column chromatography (FCC) using the indicated eluent.
91%	With sodium hydride In diethyl ether for 1h; 0 deg C to room temperature;

Reference： [1]Glas, Carina; Bracher, Franz [Synthesis, 2019, vol. 51, # 3, p. 757 - 768]
[2]Netz, David F.; Seidel, Jimmy L. [Tetrahedron Letters, 1992, vol. 33, # 15, p. 1957 - 1958]

6
[ 67442-07-3 ]
[ 122-52-1 ]
[ 124931-12-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	at 100℃; for 18h;	A solution of <strong>[67442-07-3]2-chloro-N-methoxy-N-methylacetamide</strong> (2.48 g,17.7 mmol) and triethyl phosphite (3.00 mL, 17.7 mmol) was heated to 100 °C for 18 h. The crude product was purified by flash column chromatography (0?2percent MeOH in CH2Cl2) to give 1 as a colorless oil; yield: 3.31 g (13.8 mmol; 78percent); Rf = 0.42 (2percent MeOH in CH2Cl2); HPLC purity (method b): >95percent (210 nm), >95percent (254 nm). IR (ATR): 2985, 2940, 2908, 1659, 1381, 1253, 1050, 1020, 998, 961 cm?1. 1H NMR (400 MHz, CDCl3): delta = 4.26?4.07 (m, 4 H, 2 × OCH2CH3), 3.76(s, 3 H, OCH3), 3.20 (s, 3 H, NCH3), 3.15 (d, J = 22.1 Hz, 2 H, 1-H), 1.33(td, J = 7.1, 0.6 Hz, 6 H, 2 × OCH2CH3). 13C NMR (101 MHz, CDCl3): delta = 166.2 (C-2), 62.7 (2 × OCH2CH3), 61.6(OCH3), 32.3 (NCH3), 30.9 (C-1), 16.5 (2 × OCH2CH3). HRMS (ESI): m/z [M + H]+ calcd for C8H19NO5P+: 240.0995; found: 240.0996.

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 1957 - 1958
[2]Synthesis,2019,vol. 51,p. 757 - 768
[3]Tetrahedron Letters,1989,vol. 30,p. 3779 - 3780

7
[ 124931-12-0 ]
[ 121660-37-5 ]
[ 141750-56-3 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 350 - 363

8
[ 124931-12-0 ]
[ 33603-83-7 ]
[ 180779-72-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium <i>tert</i>-butylate
80%	With potassium <i>tert</i>-butylate In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) -78 deg C, 1 h;

Reference： [1]Entwistle, David A.; Jordan, Stuart I.; Montgomery, John; Pattenden, Gerald [Journal of the Chemical Society. Perkin transactions I, 1996, # 12, p. 1315 - 1317]
[2]Entwistle, David A.; Jordan, Stuart I.; Montgomery, John; Pattenden, Gerald [Synthesis, 1998, # SPEC. ISS. APR., p. 603 - 612]

9
[ 762-04-9 ]
[ 67442-07-3 ]
[ 124931-12-0 ]

Reference： [1]Synlett,1997,p. 531 - 533

10
[ 124931-12-0 ]
[ 193337-38-1 ]
[ 193337-41-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With n-butyllithium In tetrahydrofuran at 0℃;

Reference： [1]Ouellet; Langlois; Deslongchamps, Pierre [Synlett, 1997, vol. 1997, # 6, p. 689 - 690]

11
[ 124931-12-0 ]
[ 555-16-8 ]
[ 253122-46-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium methylate In tetrahydrofuran at 20℃; for 0.333333h;

Reference： [1]Durantini, Edgardo N. [Synthetic Communications, 1999, vol. 29, # 23, p. 4201 - 4222]

12
[ 124931-12-0 ]
[ 123-11-5 ]
[ 243665-13-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at -78 - 20℃;	HWE Reaction; General Procedure A General procedure: Diethyl 2-[methoxy(methyl)amino]-2-oxoethylphosphonate (1; 1.2 equiv) was dissolved in anhyd THF and NaH (1.2 equiv) was added portionwise at r.t. until gas evolution ceased. The mixture was then cooled to -78 °C and the appropriate benzaldehyde derivative (1 equiv) dissolved in anhyd THF was added. The reaction mixture was stirred at -78 °C for 1 h, then allowed to warm to r.t. and stirred overnight. H2O (10 mL) was added, the layers were separated, and the organic layer was washed with sat. aq NaHCO3 (2 × 10 mL). The combined aqueous phases were extracted with EtOAc (3 × 15 mL). The combined organic phases were then washed with brine (2 × 10 mL) ,dried (MgSO4), and concentrated in vacuo. If necessary, the crude product was purified by flash column chromatography (FCC) using the indicated eluent.
97%	With sodium methylate In tetrahydrofuran at 20℃; for 0.333333h;
93%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at -10 - 0℃; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at -10 - 20℃; Inert atmosphere;

66%

With sodium hydride In tetrahydrofuran at -78 - 20℃; for 17h; Inert atmosphere;

Reference： [1]Glas, Carina; Bracher, Franz [Synthesis, 2019, vol. 51, # 3, p. 757 - 768]
[2]Durantini, Edgardo N. [Synthetic Communications, 1999, vol. 29, # 23, p. 4201 - 4222]
[3]Silvanus, Andrew C.; Heffernan, Stephen J.; Liptrot, David J.; Kociok-Koehn, Gabriele; Andrews, Benjamin I.; Carbery, David R. [Organic Letters, 2009, vol. 11, # 5, p. 1175 - 1178]
[4]Drissi-Amraoui, Sammy; Morin, Marie S. T.; Crévisy, Christophe; Baslé, Olivier; Marciadefigueiredo, Renata; Mauduit, Marc; Campagne, Jean-Marc [Angewandte Chemie - International Edition, 2015, vol. 54, # 40, p. 11830 - 11834][Angew. Chem., 2015, vol. 127, # 40, p. 11996 - 12000,5]

13
[ 124931-12-0 ]
(2R)-2-benzyloxycarbonylamino-3-(4-methoxybenzylsulfanyl)-succinic acid 1-methyl ester 4-tert-butyl ester [ No CAS ]
(2R,3R,4E)-3-benzyloxycarbonylamino-2-[4-methoxybenzylsulfanyl]-5-[N-methyl-N-methoxy carbamoyl]pent-4-enoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (2R)-2-benzyloxycarbonylamino-3-(4-methoxybenzylsulfanyl)-succinic acid 1-methyl ester 4-tert-butyl ester With diisobutylaluminium hydride In tetrahydrofuran; hexane; toluene at -78 - 20℃;

Reference： [1]David, Christelle; Bischoff, Laurent; Roques, Bernard P.; Fournié-Zaluski, Marie-Claude [Tetrahedron, 2000, vol. 56, # 2, p. 209 - 215]

14
[ 124931-12-0 ]
[ 23637-56-1 ]
(+/-)-N-methoxy-N-methyl-2-(2t-benzoyl-3c-phenylcycloprop-1r-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With methyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 3,6-diphenyl-3,6-dihydro-1,2-dioxine In tetrahydrofuran for 3h; Further stages.;

Reference： [1]Kimber, Marc C.; Taylor, Dennis K. [Journal of Organic Chemistry, 2002, vol. 67, # 9, p. 3142 - 3144]

15
[ 124931-12-0 ]
[ 53646-91-6 ]
trans-(+/-)-N-methoxy-N-methyl-2-(2-benzoylcyclopropyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With methyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 3-phenyl-3,6-dihydro-1,2-dioxine In tetrahydrofuran for 3h; Further stages.;

Reference： [1]Kimber, Marc C.; Taylor, Dennis K. [Journal of Organic Chemistry, 2002, vol. 67, # 9, p. 3142 - 3144]

16
[ 124931-12-0 ]
[ 445306-60-5 ]
[ 445306-61-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydride In tetrahydrofuran at 20℃;
92%	With sodium hydride In tetrahydrofuran at 20℃; for 1.5h;

Reference： [1]Mulzer, Johann; Hanbauer, Martin [Tetrahedron Letters, 2002, vol. 43, # 18, p. 3381 - 3383]
[2]Ahmed, Anjum; Hoegenauer, E. Kate; Enev, Valentin S.; Hanbauer, Martin; Kaehlig, Hanspeter; Ohler, Elisabeth; Mulzer, Johann [Journal of Organic Chemistry, 2003, vol. 68, # 8, p. 3026 - 3042]

17
[ 124931-12-0 ]
(2S,4RS)-5-(tert-butyldimethylsilyloxy)-2-methyl-4-(trimethoxymethylphenyl)pentanal [ No CAS ]
[ 478303-49-0 ]
(4S,6S)-7-(tert-butyldimethylsilyloxy)-4-methyl-6-(trimethoxymethylphenyl)hept-2-enoic acid methoxymethylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 57% 2: 35%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: (2S,4RS)-5-(tert-butyldimethylsilyloxy)-2-methyl-4-(trimethoxymethylphenyl)pentanal In tetrahydrofuran at 20℃; for 2.5h;

Reference： [1]Heckrodt, Thilo J.; Mulzer, Johann [Synthesis, 2002, # 13, p. 1857 - 1866]

18
[ 124931-12-0 ]
[ 111865-84-0 ]
[ 526217-80-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 5h;

Reference： [1]Heckrodt, Thilo J.; Mulzer, Johann [Journal of the American Chemical Society, 2003, vol. 125, # 16, p. 4680 - 4681]

19
[ 124931-12-0 ]
C₂₈H₄₄O₁₀ [ No CAS ]
C₃₂H₅₁NO₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.171 g	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: C₂₈H₄₄O₁₀ In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Zakarian, Armen; Batch, Alexandre; Holton, Robert A. [Journal of the American Chemical Society, 2003, vol. 125, # 26, p. 7822 - 7824]

20
[ 124931-12-0 ]
[ 623151-46-2 ]
[ 623151-47-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.16667h; Stage #2: (5Z,7E)-(3R,4R)-4-(tert-butyldimethylsilanyloxy)-10-(tert-butyldiphenylsilanyloxy)-3-methyldeca-5,7-dienal In tetrahydrofuran at 20℃; for 1.16667h;

Reference： [1]Dineen, Thomas A.; Roush, William R. [Organic Letters, 2003, vol. 5, # 24, p. 4725 - 4728]

21
[ 862893-91-2 ]
[ 124931-12-0 ]
[ 862893-92-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 20℃; for 2h;

Reference： [1]Sohn, Stephanie S.; Bode, Jeffrey W. [Organic Letters, 2005, vol. 7, # 18, p. 3873 - 3876]

22
[ 863407-41-4 ]
[ 124931-12-0 ]
[ 863407-46-9 ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: [6-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde In tetrahydrofuran at 0℃;

Reference： [1]Mattson, Ronald J.; Catt, John D.; Denhart, Derek J.; Deskus, Jeffrey A.; Ditta, Jonathan L.; Higgins, Mendi A.; Marcin, Lawrence R.; Sloan, Charles P.; Beno, Brett R.; Gao, Qi; Cunningham, Melissa A.; Mattson, Gail K.; Molski, Thaddeus F.; Taber, Matthew T.; Lodge, Nicholas J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6023 - 6034]

23
[ 863407-42-5 ]
[ 124931-12-0 ]
[ 863407-47-0 ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: [4-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde In tetrahydrofuran at 0℃;

24
[ 863407-40-3 ]
[ 124931-12-0 ]
[ 863407-45-8 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: [7-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde In tetrahydrofuran at 0℃;

25
[ 468718-26-5 ]
[ 124931-12-0 ]
[ 468718-27-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 3-formyl-1-(4-toluenesulfonyl)-1H-indole-6-carbonitrile In tetrahydrofuran at 0℃;

26
[ 863407-39-0 ]
[ 124931-12-0 ]
[ 863407-44-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 3-formyl-1-(4-toluenesulfonyl)-1H-indole-4-carbonitrile In tetrahydrofuran at 0℃;

27
[ 468717-73-9 ]
[ 124931-12-0 ]
[ 468717-74-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: 3-formyl-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile In tetrahydrofuran at 0℃; for 1h;

28
[ 863407-38-9 ]
[ 124931-12-0 ]
[ 863407-43-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 3-formyl-1-(4-toluenesulfonyl)-1H-indole-7-carbonitrile In tetrahydrofuran at 0℃;

29
[ 124931-12-0 ]
[ 217489-00-4 ]
[ 468717-78-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 5-fluoro-1-(p-tolylsulfonyl)indole-3-carboxaldehyde In tetrahydrofuran at 0℃;
88%	In tetrahydrofuran	2 Trans-1-(N,N-dimethylaminomethyl)-2-[5-fluoroindol-3-yl]cyclopropane A solution of diethyl (N-methoxy-N-methylcarbamoylmethyl) phosphonate (5.64 ml, 6.54 g, 27.4 mmol) in anhydrous tetrahydrofuran (25 ml) was added to a stirred suspension of oil free sodium hydride (1.05 g, 27.4 mmol) in anhydrous tetrahydrofuran (350 ml) maintained at 0° C. The reaction was warmed to room temperature and was stirred for 2 h. After cooling to 0° C., [5-fluoro-1-(p-toluenesulfonyl)indol-3-yl]carboxaldehyde (7.24 g, 22.8 mmol) was added. The resulting mixture was stirred at 0° C. for 30 min. The reaction was quenched with aqueous hydrochloric acid (0.1 N) and poured into water (150 ml). After being made acidic with hydrochloric acid (1.0 N), the aqueous portion was extracted with ethyl acetate (3*100 ml). The combined organic layers were washed with brine (50 ml) and dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo. The crude product was purified by recrystallization from ethyl acetate to afford a total of 8.03 g (88% yield) of (E)-[5-fluoro-1-(p-toluenesulfonyl)indol-3-yl]-N-methoxy-N-methylacrylamide as a white solid: mp 199-200° C. (dec.); 1H NMR (400 MHz, DMSO-d6) 8.56 (1 H, s), 7.99 (1 H, m), 7.93 (2 H, d, J=8.4 Hz), 7.68 (2 H, m), 7.42 (2 H, d, J=8.1 Hz), 7.28 (1 H, t, J=9.2 Hz), 7.12 (1 H, d, J=16 Hz), 3.77 (3 H, s), 3.22 (3 H, s), 2.33 (3 H, s); MS m/e 403 (M+H)+. Anal. Calcd. For C20H19FN2O4S: C, 59.69; H, 4.75; N 6.96. Found: C, 59.60; H, 4.70; N, 6.86.

30
[ 124931-12-0 ]
[ 1489-69-6 ]
[ 141580-89-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: Cyclopropanecarboxaldehyde In tetrahydrofuran at 20℃; for 2h; Further stages.;
79%	Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Cyclopropanecarboxaldehyde In tetrahydrofuran at 20℃; for 4h;

Reference： [1]Wender, Paul A.; Fuji, Masahiro; Husfeld, Craig O.; Love, Jennifer A. [Organic Letters, 1999, vol. 1, # 1, p. 137 - 139]
[2]Trost, Barry M.; Shen, Hong C.; Horne, Daniel B.; Toste, F. Dean; Steinmetz, Bernhard G.; Koradin, Christopher [Chemistry - A European Journal, 2005, vol. 11, # 8, p. 2577 - 2590]

31
[ 20780-76-1 ]
[ 124931-12-0 ]
(E)-2-(5-iodo-2-oxoindolin-3-ylidene)-N-methoxy-N-methylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 18h;

Reference： [1]Chen, Chuo; Li, Xiaodong; Neumann, Christopher S.; Lo, Michael M.-C.; Schreiber, Stuart L. [Angewandte Chemie - International Edition, 2005, vol. 44, # 15, p. 2249 - 2252]

32
[ 124931-12-0 ]
[ 689258-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	With NaH In tetrahydrofuran	63.3 (2-{2,3-Difluoro-4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl}cyclopropyl)acetic acid Trifluoroacetate. Step 3: (2E)-3-(2,3-Difluoro-4-methoxyphenyl)-N-methoxy-N-methylprop-2-enamide. Diethyl (N-methoxy-N-methylcarbamoylmethyl)-phosphonate (4.8 g) was added to a suspension of 95% NaH (550 mg) in THF (40 mL) under nitrogen atmosphere. The mixture was stirred at an ambient temperature for 10 minutes, and was treated with the product of step 2 (3.44 grams). The mixture was stirred at room temperature for 1 hour and was quenched with water (10 mL). The mixture was concentrated in vacuoo afforded an oily residue. The residue was extracted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated to yield 3.2 grams of the title compound as white solid. 1H-NMR(CDCl3): 7.72 (d, 1H), 7.22(m, 1H), 7.15(d, 1H), 6.75(m,1H), 3.92(s, 3H), 3.78(s, 3H), 3.3(s, 3H).

Reference： [1]Current Patent Assignee: PFIZER INC - US6921767, 2005, B2

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[ CAS No. 124931-12-0 ]

Quality Control of [ 124931-12-0 ]

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Product Details of [ 124931-12-0 ]

Safety of [ 124931-12-0 ]

Application In Synthesis of [ 124931-12-0 ]

[ 124931-12-0 ] Synthesis Path-Downstream 1~32

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