[ CAS No. 37988-38-8 ] {[proInfo.proName]}

Name: 37988-38-8|2-(Pyridin-2-yl)propan-2-ol|97%
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SKU: A131849
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Quality Control of [ 37988-38-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 37988-38-8 ]

Product Details of [ 37988-38-8 ]

CAS No. :	37988-38-8	MDL No. :	MFCD00209259
Formula :	C₈H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LUZJNRNNOOBBDY-UHFFFAOYSA-N
M.W :	137.18	Pubchem ID :	2779146
Synonyms :

Calculated chemistry of [ 37988-38-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.38
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.86
TPSA :	33.12 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.63
Log Po/w (XLOGP3) :	0.59
Log Po/w (WLOGP) :	1.2
Log Po/w (MLOGP) :	0.55
Log Po/w (SILICOS-IT) :	1.5
Consensus Log Po/w :	1.09

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.44
Solubility :	4.98 mg/ml ; 0.0363 mol/l
Class :	Very soluble
Log S (Ali) :	-0.86
Solubility :	19.0 mg/ml ; 0.138 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.24
Solubility :	0.784 mg/ml ; 0.00571 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.33

Safety of [ 37988-38-8 ]

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 [ 37988-38-8 ]

* 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.

Upstream synthesis route of [ 37988-38-8 ]
Downstream synthetic route of [ 37988-38-8 ]

[ 37988-38-8 ] Synthesis Path-Upstream 1~14

1
[ 37988-38-8 ]
[ 75-24-1 ]
[ 5944-41-2 ]
[ 6515-13-5 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3127 - 3133

2
[ 91-02-1 ]
[ 917-54-4 ]
[ 37988-38-8 ]
[ 19490-92-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	at -78 - 20℃; for 1.25 h;	[00151] Example 8. Synthesis of 2-(pyridin-2-yl)propan-2-ol (PyPrOH) and I -phenyl- 1 - (pyridin-2-yl)ethanol (PPE). The appropriate ketone Py(CQ)(L) (8.3 mmol) was dissolved in dry diethyl ether (100 mL) in an oven-dried 250 mL schlenk flask. This was cooled to -78° C and MeLi (12.9 mL of a 1.6M solution) was added slowly over 15 minutes. The resulting yellow solution was stirred at -78° C for 1 hour, and was then warmed to ambient temperature. Next, saturated NH₄C1 (aq) (30 mL) was added to quench the reaction, and the resulting solution was extracted with EtOAc (3 x 75 mL), dried over Na₂S0₄, and the solvent evaporated in vacuo. The crude product was purified via flash chromatography (Si0₂, 1 : 1 EtOAc:CH₂Cl₂ for L=Me, 1 :3 EtOAc:CH₂Cl₂ for L=Ph) to yield a light yellow oil. PyPrOH was obtained (yield: 55percent). PyPrOH: 1H NMR NMR (CDCL, 300 MHz): δ 8.52 (d of m, J= 4.8 Hz, 1 H); 7.71 (t of m, J = 7.8 Hz, 1 H): 7.38 (d of m, J= 8.1 Hz, ): 7.21 (t of m, J= 6.2 Hz, i l l ): 5.08 (s, 1H); 1.54 (s, 6H). PPE was obtained (yield: 97percent). 1H NMR (CDC1₃, 300 MHz): δ 8.52 (d of m, J= 5.1 Hz, 1 H): 7.65 (t of d, J= 7.8 Hz, 1.8 Hz, 1 H); 7.48 (m, 2H); 7.31 (m, 3H); 7.17- 7.26 (m, 2H); 5.85 (s, 1H); 1.94 (s, 3H).

Reference： [1] Patent: WO2014/200497, 2014, A1, . Location in patent: Paragraph 00151

3
[ 109-04-6 ]
[ 67-64-1 ]
[ 37988-38-8 ]

Reference： [1] Tetrahedron Letters, 1999, vol. 40, # 23, p. 4339 - 4342
[2] Tetrahedron, 2000, vol. 56, # 10, p. 1349 - 1360
[3] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1992, # 12, p. 1949 - 1956

4
[ 2524-52-9 ]
[ 917-54-4 ]
[ 37988-38-8 ]

Reference： [1] Patent: WO2014/145051, 2014, A1, . Location in patent: Paragraph 0337

5
[ 1122-62-9 ]
[ 917-64-6 ]
[ 37988-38-8 ]

Reference： [1] New Journal of Chemistry, 2001, vol. 25, # 2, p. 353 - 357
[2] Dalton Transactions, 2018, vol. 47, # 29, p. 9701 - 9708

6
[ 110-86-1 ]
[ 67-64-1 ]
[ 37988-38-8 ]

Reference： [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 24, p. 3597 - 3600
[2] Journal of the American Chemical Society, 1948, vol. 70, p. 2381,2383
[3] Kogyo Kagaku Zasshi, 1954, vol. 57, p. 902[4] Chem.Abstr., 1956, p. 999
[5] Chemische Berichte, 1939, vol. 72, p. 1188,1193
[6] Journal of Organic Chemistry, 1957, vol. 22, p. 1296,1300,1301

7
[ 1122-62-9 ]
[ 75-16-1 ]
[ 37988-38-8 ]

Reference： [1] Organometallics, 2017, vol. 36, # 18, p. 3578 - 3588

8
[ 1122-62-9 ]
[ 37988-38-8 ]

Reference： [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 18, p. 3607 - 3612

9
[ 1122-62-9 ]
[ 37988-38-8 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3127 - 3133

10
[ 1122-62-9 ]
[ 917-54-4 ]
[ 37988-38-8 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 213 - 220
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 213 - 220
[3] Journal of the American Chemical Society, 2014, vol. 136, # 40, p. 14160 - 14172
[4] Journal of Physical Organic Chemistry, 2006, vol. 19, # 5, p. 295 - 307

11
[ 1122-62-9 ]
[ 676-58-4 ]
[ 37988-38-8 ]

Reference： [1] New Journal of Chemistry, 2017, vol. 41, # 14, p. 6709 - 6719

12
[ 917-64-6 ]
[ 2524-52-9 ]
[ 37988-38-8 ]

Reference： [1] Chemische Berichte, 1908, vol. 41, p. 4103

13
[ 1122-62-9 ]
[ 74-83-9 ]
[ 37988-38-8 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1989, # 4, p. 818 - 834

14
[ 17624-36-1 ]
[ 67-64-1 ]
[ 37988-38-8 ]

Reference： [1] Canadian Journal of Chemistry, 1981, vol. 59, p. 65 - 75

[ 37988-38-8 ] Synthesis Path-Downstream 1~88

1
[ 110-86-1 ]
[ 67-64-1 ]
[ 37988-38-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 3597 - 3600
[2]Journal of the American Chemical Society,1948,vol. 70,p. 2381,2383
[3]Journal of Organic Chemistry,1957,vol. 22,p. 1296,1300,1301

2
[ 917-64-6 ]
[ 2524-52-9 ]
[ 37988-38-8 ]

Reference： [1]Chemische Berichte,1908,vol. 41,p. 4103

3
[ 17624-36-1 ]
[ 67-64-1 ]
[ 37988-38-8 ]

Reference： [1]Canadian Journal of Chemistry,1981,vol. 59,p. 65 - 75

5
[ 1122-62-9 ]
[ 917-54-4 ]
[ 37988-38-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 213 - 220
[2]Journal of the Chemical Society. Perkin transactions I,1985,p. 213 - 220
[3]Journal of the American Chemical Society,2014,vol. 136,p. 14160 - 14172
[4]Journal of Physical Organic Chemistry,2006,vol. 19,p. 295 - 307

6
[ 1122-62-9 ]
[ 74-83-9 ]
[ 37988-38-8 ]

Reference： [1]Journal of Chemical Research, Miniprint,1989,p. 818 - 834

7
[ 37988-38-8 ]
[ 20603-17-2 ]

Reference： [1]Journal of Chemical Research, Miniprint,1989,p. 818 - 834

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE I STR8 2-Acetylpyrazine (12.2 g, 0.1 mole) was dissolved in tetrahydrofuran (140 mL). 1,10-phenanthrolin was added as an indicator, and the solution was cooled to -30 C. Methyllithium (1.5M in hexane) was added dropwise through an addition funnel over a 30 minute period while maintaining the temperature at <-20 C., and about 60 mL of methyllithium was used to reach a dark colored end point. The mixture was stirred at this temperature for 30 minutes, and then was poured into ice water (200 g). The organic layer was separated and the aqueous layer was extracted with hexane (4100 mL) and ether (5100 mL). The combined organic solution was dried with anhydrous MgSO4. Gas Chromatographic analysis indicates a 47:53 ratio of acetylpyrazine to product. The solvent was removed by rotary evaporation under aspirator vacuum to provide a light yellow liquid. An analytical pure sample of the 2-pyrazinyl-2-propanol product was isolated by preparative gas chromatography. NMR and IR spectra confirmed the structure of the title compound. 2-Pyridinyl-2-propanol is prepared by using 2-acetylpyridine in place of 2-acetylpyrazine.

10
[ 1122-62-9 ]
Me4(PrO)4(μ-PrO)2W2 [ No CAS ]
[ 37988-38-8 ]

Reference： [1]Chemische Berichte,1993,vol. 126,p. 2083 - 2092

11
[ 110-86-1 ]
[ 67-64-1 ]
magnesium [ No CAS ]
mercury (II)-chloride [ No CAS ]
[ 37988-38-8 ]

Reference： [1]Chemische Berichte,1939,vol. 72,p. 1188,1193

12
[ 1122-62-9 ]
[ 917-64-6 ]
[ 37988-38-8 ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 353 - 357
[2]Dalton Transactions,2018,vol. 47,p. 9701 - 9708

13
[ 37988-38-8 ]
[ 6581-08-4 ]

Reference： [1]Dalton Transactions,2004,p. 1539 - 1545
[2]Journal of Organic Chemistry,2012,vol. 77,p. 3127 - 3133

14
[ 37988-38-8 ]
phenyl-phosphonic acid mono-(1-methyl-1-pyridin-2-yl-ethyl) ester [ No CAS ]

Reference： [1]Dalton Transactions,2004,p. 1539 - 1545

15
[ 37988-38-8 ]
C₂₂H₂₅N₂O₂P*ClH [ No CAS ]

Reference： [1]Dalton Transactions,2004,p. 1539 - 1545

16
[ 37988-38-8 ]
ammonium hexafluorophosphate [ No CAS ]
cis-dichlorobis(2,2'-bipyridine)ruthenium(II) dihydrate [ No CAS ]
bis(2,2'-bipyridine){2-(2-pyridyl)propan-2-ol}ruthenium(II) hexafluorophosphate [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1992,p. 1949 - 1956

17
[ 37988-38-8 ]
[ 41924-26-9 ]
bis((trimethylsilyl)methyl)zinc(2-(2-pyridyl)2-propoxide) [ No CAS ]

Reference： [1]Organometallics,1993,vol. 12,p. 3624 - 3629

18
[ 37988-38-8 ]
MoCl₂(N(2,6-i-Pr₂C₆H₃))2(1,2-dimethoxyethane) [ No CAS ]
Mo(C₆H₃(C₃H₇)2)2Cl(2-pyridyldimethylmethoxide) [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,1999,p. 1727 - 1733

19
[ 37988-38-8 ]
WO₂(CH₃COCH₂COCH₃)2 [ No CAS ]
dioxobis[2-(2'-pyridyl)propan-2-olato-N,O]tungsten(VI) [ No CAS ]

Reference： [1]New Journal of Chemistry,1999,vol. 23,p. 5 - 7

20
[ 37988-38-8 ]
[ 24356-01-2 ]
Zr(CH₂C₆H₅)2(C₅H₄NC(CH₃)2O)2 [ No CAS ]

Reference： [1]Organometallics,1997,vol. 16,p. 3303 - 3313

21
[ 37988-38-8 ]
tungsten dioxide dichloride [ No CAS ]
dioxobis[2-(2'-pyridyl)propan-2-olato-N,O]tungsten(VI) [ No CAS ]

Reference： [1]New Journal of Chemistry,1999,vol. 23,p. 5 - 7

22
[ 37988-38-8 ]
[ 139467-76-8 ]
dioxotungsten(VI)[C₅H₄NCOMe₂]2 [ No CAS ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 353 - 357

23
[ 37988-38-8 ]
[ 29046-78-4 ]
[Ni2(μ-Cl)2(2-pyridin-2-ylpropan-2-ol)2]Cl2 [ No CAS ]

Reference： [1]Inorganic Chemistry,2004,vol. 43,p. 4234 - 4240

24
[ 37988-38-8 ]
bis(acetylacetonato)dioxidomolybdenum(VI) [ No CAS ]
[ 188734-73-8 ]

Reference： [1]Journal of Molecular Catalysis A: Chemical,1997,vol. 117,p. 455 - 469

25
[ 37988-38-8 ]
[ 3375-31-3 ]
[ 1000169-08-3 ]

Reference： [1]Organometallics,2007,vol. 26,p. 6290 - 6299

26
[ 37988-38-8 ]
[ 53675-30-2 ]
bis(N,O-[2-(2'-pyridyl)propan-2-olato])chlorooxorhenium(V) [ No CAS ]

Reference： [1]Organometallics,2007,vol. 26,p. 6290 - 6299

27
[ 37988-38-8 ]
[ 53675-30-2 ]
tetrabutylammonium-cis([N,O-(2-(2'-pyridyl)propan-2-olato)]trichlorooxorhenate(V)) [ No CAS ]

Reference： [1]Organometallics,2007,vol. 26,p. 6290 - 6299
[2]Organometallics,2007,vol. 26,p. 6290 - 6299

28
[ 37988-38-8 ]
[ 54935-70-5 ]
[W₂(2-(2-pyridyl)propan-2-ol(-H))2(NMe₂)4] [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2007,p. 5541 - 5547

29
[ 37988-38-8 ]
[ 26042-63-7 ]
[Rh₂Cl₂(1,2-bis(tert-butylsulfinyl)ethane)2] [ No CAS ]
[Rh(1,2-bis(tert-butylsulfinyl)ethane)(2-hydroxyisopropylpyridine)]PF₆ [ No CAS ]

Reference： [1]Inorganic Chemistry,2008,vol. 47,p. 6502 - 6512

30
[ 37988-38-8 ]
[Rh₂Cl₂(1,2-bis(tert-butylsulfinyl)ethane)2] [ No CAS ]
[ 2923-28-6 ]
[Rh(1,2-bis(tert-butylsulfinyl)ethane)(2-hydroxyisopropylpyridine)][CF₃SO₃] [ No CAS ]

Reference： [1]Inorganic Chemistry,2008,vol. 47,p. 6502 - 6512

31
[ 37988-38-8 ]
[Ir₂Cl₂(1,2-bis(tert-butylsulfinyl)ethane)2] [ No CAS ]
[IrHCl(1,2-bis(tert-butylsulfinyl)ethane)(2-hydroxyisopropylpyridine(-H))] [ No CAS ]

Reference： [1]Inorganic Chemistry,2008,vol. 47,p. 6502 - 6512

32
[ 37988-38-8 ]
manganese(II) chloride tetrahydrate [ No CAS ]
sodium trimethylacetate monohydrate [ No CAS ]
[ 75-05-8 ]
[Mn₇O₃(OH)3(O₂C-t-Bu)7(2-(pyridine-2-yl)propan-2-ol(-1H))4]*CH₃CN [ No CAS ]

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 199 - 208

33
[ 37988-38-8 ]
[ 636-13-5 ]
[Mn₁₂O₇(OH)(OMe)2(O₂CPh)12(2-(pyridine-2-yl)propan-2-ol(-1H))4(H₂O)]*3H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 199 - 208
[2]Inorganic Chemistry,2010,vol. 49,p. 199 - 208

34
[ 37988-38-8 ]
[ 12354-84-6 ]
[ 7732-18-5 ]
(η5-C5Me5)Ir(2-(2'-pyridyl)-2-propanolate)Cl*0.67H2O [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 10473 - 10481
[2]Journal of the American Chemical Society,2011,vol. 133,p. 10473 - 10481

35
[ 1122-62-9 ]
lithium trimethylmagnesate [ No CAS ]
[ 37988-38-8 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 3127 - 3133

36
[ 37988-38-8 ]
[ 75-24-1 ]
[ 5944-41-2 ]
[ 6515-13-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 3127 - 3133

37
[ 37988-38-8 ]
[ 644-98-4 ]

Reference： [1]International Journal of Mass Spectrometry,2011,vol. 306,p. 159 - 166

38
[ 37988-38-8 ]
N-benzyl-2-isopropylpyridinium bromide [ No CAS ]

Reference： [1]International Journal of Mass Spectrometry,2011,vol. 306,p. 159 - 166

39
[ 37988-38-8 ]
(η5-C5Me5)Ir(μ-OH)3Ir(η5-C5Me5)OH [ No CAS ]
[ 1380109-07-8 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 9785 - 9795

40
[ 37988-38-8 ]
[ 109-72-8 ]
[ 1402918-48-2 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 5400 - 5403,4

41
[ 37988-38-8 ]
C₄₈H₇₁Cl₂N₄PRu [ No CAS ]
C₃₈H₄₈ClN₅ORu [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 14717 - 14724

42
[ 37988-38-8 ]
C₄₈H₇₁Cl₂N₄PRuS [ No CAS ]
C₃₈H₄₈ClN₅ORuS [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 14717 - 14724

43
[ 17084-13-8 ]
[ 37988-38-8 ]
[ 12354-84-6 ]
(η⁵-C₅Me₅)Ir(2-(2-pyridyl)-2-propanolate)PF₆ [ No CAS ]

Reference： [1]Inorganic Chemistry,2012,vol. 51,p. 12313 - 12323

44
[ 37988-38-8 ]
[ 12354-84-6 ]
[ 143-66-8 ]
(η⁵-C₅Me₅)Ir(2-(2-pyridyl)-2-propanolate)BPh₄ [ No CAS ]

Reference： [1]Inorganic Chemistry,2012,vol. 51,p. 12313 - 12323

45
[ 37988-38-8 ]
[ 12112-67-3 ]
[ 1446713-80-9 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 10837 - 10851

46
[ 246047-72-3 ]
[ 37988-38-8 ]
benzylidene-chloro(1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)-[1-(2′-pyridinyl)-propane-2-olato]ruthenium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of lithium alcoholate (0.63 mmol, 0.090 g) in THF (5 mL) was added dropwise to a solution of 2 (0.55 mmol, 0.470 g) in THF (5-10 mL) under inert (Ar) and very dry conditions. The reaction was stirred at 30-40 C for 60 min with a colour change from brown to various shades of green. The progress of the reaction was monitored by TLC (Merck Silica gel 60 F254; eluent hexane-ethyl acetate = 1:2) to determine if the starting complex was being consumed. The reaction mixture was stirred until the TLC indicated that the starting complex was not present any more. After removing the solvent under vacuum the residue was dissolved in a minimal amount of toluene. The lithium chloride was then removed by filtration via a syringe filter and the solution concentrated to a volumeof ca. 1 mL. The complexes were obtained by adding 10-15 mL cold pentane onto the filtrate and placing it in the fridge for 8 h or by immediate sonification for 10 min resulting in the immediate formation of a precipitate. After removal of the pentane via syringe or filtration, the desired complex was washed with cold pentane to produce analytically pure microcrystalline powders.

Reference： [1]Molecules,2014,vol. 19,p. 5522 - 5537

47
[ 37988-38-8 ]
4-(3-iodo-1H-pyrrolo[3,2-b]pyridin-6-yl)-3,5-dimethylisoxazole [ No CAS ]
4-[3-iodo-1-[1-methyl-1-(2-pyridyl)ethyl]pyrrolo[3,2-b]pyridin-6-yl]-3,5-dimethylisoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.6 g	With ethyl (NE)-N-ethoxycarbonyliminocarbamate; phenyl diphenylphosphinite; In tetrahydrofuran; toluene; at 20 - 65℃; for 4.25h;Cooling with ice;	To 4-(3-iodo-lH-pyrrolo[3,2-b]pyridin-6-yl)-3,5-dimethyl-isoxazole (P- 0072, 1.26 g, 3.73 mmol) in THF (20 ml) was added 2-(2-pyridyl)propan-2-ol (56) (0.91 g, 6.63 mmol) and phenoxy(diphenyl)phosphane (1.89 g, 6.77 mmol). The reaction was cooled with an ice water bath, followed by the addition of 2.3M ethyl (NE)-N-ethoxycarbonyliminocarbamate in toluene (2.94 ml) dropwise over 15 minutes. After 1 hour, the reaction was removed from the ice bath and allowed to warm to room temperature for 1 hour. The reaction was heated to 65 C for 2 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and filtered. The filtrate was concentrated, and purified by silica gel flash chromatography eluting with 20- 100% ethyl acetate in hexane to give impure product that was used without further purification (57, 0.6 g, -35%).

Reference： [1]Patent: WO2014/145051,2014,A1 .Location in patent: Paragraph 0338

48
[ 2524-52-9 ]
[ 917-54-4 ]
[ 37988-38-8 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; diethyl ether; at -78℃; for 3h;	To a solution of ethyl pyridine-2- carboxylate (5 g, 33.08 mmol) in THF ( 50 ml) cooled to -78 C was added 1.6M methyllithium in ether (50 ml) slowly. After 3 hours, the reaction mixture was allowed to warm to room temperature for 10 minutes. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give crude product (56, 4.0 g, 88.2%) which was used in the next step without further purification.

Reference： [1]Patent: WO2014/145051,2014,A1 .Location in patent: Paragraph 0337

49
[ 37988-38-8 ]
methyl 4-[6-(3,5-dimethylisoxazol-4-yl)-1-[1-methyl-1-(2-pyridyl)ethyl]pyrrolo[3,2-b]pyridin-3-yl]benzoate [ No CAS ]

Reference： [1]Patent: WO2014/145051,2014,A1

50
[ 37988-38-8 ]
4-[6-(3,5-dimethylisoxazol-4-yl)-1-[1-methyl-1-(2-pyridyl)ethyl]pyrrolo[3,2-b]pyridin-3-yl]benzoic acid [ No CAS ]

Reference： [1]Patent: WO2014/145051,2014,A1

51
[ 37988-38-8 ]
[Rh(5,6-chrysenequinone diimmine)(1,10-phenanthroline)(NH₃)₂]TFA₃ [ No CAS ]
[ 7786-30-3 ]
[Rh(5,6-chrysenequinone diimmine)(1,10-phenanthroline)(2-(pyridine-2-yl)propan-2-ol)]Cl₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 14160 - 14172

52
[ 37988-38-8 ]
[Rh(5,6-chrysenequinone diimmine)(1,10-phenanthroline)(NH₃)₂]TFA₃ [ No CAS ]
[Rh(chrysi)(phen)(PyPrO)]TFA₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; at 98℃; for 18h;	[00181] Example 24, Synthesis of [Rh(chrysi)(phen)(PPE)]2+ and [Rh(chrysi)(phen)(PyPrO)]2+- [Rh(chrysi)(phen)(NH3)2]TFA3 (at 62.3 mg, 0.092 mmol) and (PPE or PyPrO) (at 0.138 mmol) were dissolved in 1 : 12 H20:EtOH (90 mL). The resulting red solution was heated to 98s C and refluxed for 18 hours. The resulting solution was dried in vacuo, redissolved in H20 (10 mL), filtered, and purified via flash chromatography (Cjg-SiO?, 17:3 0.1% TFA (aq): MeCN). PyPrO: ESI-MS (cation): m/z caic 674.1 (M - 1H+), 337.6 (M2+), obs. 674.0, 337.7. UV-Vis (H20, pH 7): 270 nm (122,400 M" cm"1), 300 nm (41,600 M"1 cm 1), 430 nm (12,300 M"1 cm 1). PPE: ESI-MS (cation): m/z caic 736.2 (M - IH+), 368.6 (M2+), obs. 736.0, 368.8. UV-Vis (H20, pH 7): 270 nm (165,800 M"1 cm" 1), 300 nm (56,300 M"1 cm"1), 430 nm (16,100 M" 1 cm"1). (Mixture of tw o isomers were obtained.)

Reference： [1]Patent: WO2014/200497,2014,A1 .Location in patent: Paragraph 0092; 00181

53
[ 91-02-1 ]
[ 917-54-4 ]
[ 37988-38-8 ]
[ 19490-92-7 ]

Yield	Reaction Conditions	Operation in experiment
55%; 97%	In diethyl ether; at -78 - 20℃; for 1.25h;	[00151] Example 8. Synthesis of 2-(pyridin-2-yl)propan-2-ol (PyPrOH) and I -phenyl- 1 - (pyridin-2-yl)ethanol (PPE). The appropriate ketone Py(CQ)(L) (8.3 mmol) was dissolved in dry diethyl ether (100 mL) in an oven-dried 250 mL schlenk flask. This was cooled to -78 C and MeLi (12.9 mL of a 1.6M solution) was added slowly over 15 minutes. The resulting yellow solution was stirred at -78 C for 1 hour, and was then warmed to ambient temperature. Next, saturated NH4C1 (aq) (30 mL) was added to quench the reaction, and the resulting solution was extracted with EtOAc (3 x 75 mL), dried over Na2S04, and the solvent evaporated in vacuo. The crude product was purified via flash chromatography (Si02, 1 : 1 EtOAc:CH2Cl2 for L=Me, 1 :3 EtOAc:CH2Cl2 for L=Ph) to yield a light yellow oil. PyPrOH was obtained (yield: 55%). PyPrOH: 1H NMR NMR (CDCL, 300 MHz): delta 8.52 (d of m, J= 4.8 Hz, 1 H); 7.71 (t of m, J = 7.8 Hz, 1 H): 7.38 (d of m, J= 8.1 Hz, ): 7.21 (t of m, J= 6.2 Hz, i l l ): 5.08 (s, 1H); 1.54 (s, 6H). PPE was obtained (yield: 97%). 1H NMR (CDC13, 300 MHz): delta 8.52 (d of m, J= 5.1 Hz, 1 H): 7.65 (t of d, J= 7.8 Hz, 1.8 Hz, 1 H); 7.48 (m, 2H); 7.31 (m, 3H); 7.17- 7.26 (m, 2H); 5.85 (s, 1H); 1.94 (s, 3H).

Reference： [1]Patent: WO2014/200497,2014,A1 .Location in patent: Paragraph 00151

54
[ 37988-38-8 ]
[(η₅-pentamethylcyclopentadienyl)₂Ir₂(μ-OH)₃]OH [ No CAS ]
[ 1380109-07-8 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 13826 - 13834
[2]Inorganic Chemistry,2019,vol. 58,p. 16537 - 16545

55
[ 37988-38-8 ]
[ 12112-67-3 ]
[(η²-cis-cis-1,5-cyclooctadiene)Ir^I(2-(2'-pyridyl)-2-propanolate-κO,κN)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With n-butyllithium; In tetrahydrofuran; hexane; at 20℃; for 0.166667h;Inert atmosphere;	2-(2'pyridyl)-2-propanol (28 mg, 0.2 mmol) was dissolved in dry THF (10 mL) and n-butyllithium in hexanes (125 muL of a 1.6 M solution, 0.2 mmol) was added drop wise at room temperature. The clear, colorless solution was then added to a solution of [(cod)IrCl]2 (67 mg, 0.1 mmol) in dry THF (10 mL) via cannula, causing an gradual color change from orange to yellow. The solution was stirred for 10 minutes at room temperature and then taken to dryness under reduced pressure. Et2O was added (10 mL) to the solid residue, the mixture briefly sonicated, and filtered through 0.2 mum pore size Teflon filter. Evaporation of solvent under reduced pressure and drying in vacuo yielded a yellow-orange powder. Yield=74 mg (85%). 1H-NMR (400 MHz, CD2Cl2): delta=7.92 (d, J=5.6 Hz, 1H), 7.80 (td, J=7.9 Hz, J=1.5 Hz, 1H), 7.43 (d, J=8.1 Hz, 1H), 7.20 (ddd, J=7.2 Hz, J=5.7 Hz, J=1.3 Hz, 1H), 4.15 (m, 2H), 3.11 (m, 2H), 2.24 (m, 4H), 1.68 (m, 4H), 1.48 (s, 6H). 13C-NMR (126 MHz, CD2-Cl2): delta=183.0, 146.9, 138.3, 123.1, 122.6, 86.9, 68.1, 52.8, 34.7, 32.7, 31.8. ESI(+) MS calcd for C16H21IrNO+: 434.123, 436.126. Found: m/z=434.122, 436.125.

Reference： [1]Patent: US2015/21194,2015,A1 .Location in patent: Paragraph 0102
[2]Inorganic Chemistry,2016,vol. 55,p. 2427 - 2435

56
[ 17084-13-8 ]
[ 37988-38-8 ]
iridium(III) chloride monohydrate [ No CAS ]
mer-tris(2-{pyridin-2-yl}propan-2-olato)iridium(IV) hexafluorophosphate [ No CAS ]
fac-tris(2-{pyridin-2-yl}propan-2-olato)iridium(III) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 7243 - 7250

57
[ 37988-38-8 ]
rhodium(III) trichloride hydrate [ No CAS ]
[ 7732-18-5 ]
mer-tris(2-{pyridin-2-yl}propan-2-olato)rhodium(III) monohydrate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 15692 - 15695

58
[ 37988-38-8 ]
iridium(III) chloride trihydrate [ No CAS ]
cis-Cl,cis-O,trans-N-[bis(2-{pyridin-2-yl}propan-2-olato)dichloroiridium(IV)] [ No CAS ]
cis-Cl,cis-O,cis-N-[bis(2-{pyridin-2-yl}propan-2-olato)dichloroiridium(IV)] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 15917 - 15926

59
[ 586-98-1 ]
[ 37988-38-8 ]
2,5-bis(N-((S)-1-phenylethyl)aldimino)pyrrole [ No CAS ]
[ 1184-54-9 ]
C₅₈H₆₀Cu₂N₈O₂ [ No CAS ]

Reference： [1]ACS Catalysis,2017,vol. 7,p. 6289 - 6301

60
[ 37988-38-8 ]
[ 75-09-2 ]
2,5-bis(N-((S)-1-phenylethyl)aldimino)pyrrole [ No CAS ]
[ 1184-54-9 ]
3C₂₂H₂₂N₃^(1-)*4Cu⁽²⁺⁾*Cl^(1-)*4C₈H₁₀NO^(1-) [ No CAS ]

Reference： [1]ACS Catalysis,2017,vol. 7,p. 6289 - 6301

61
[ 37988-38-8 ]
[ 12354-84-6 ]
[ 1312545-14-4 ]

Reference： [1]Organometallics,2017,vol. 36,p. 3578 - 3588
[2]ChemCatChem,2018,vol. 10,p. 4280 - 4291

62
[ 1122-62-9 ]
[ 75-16-1 ]
[ 37988-38-8 ]

Reference： [1]Organometallics,2017,vol. 36,p. 3578 - 3588
[2]Inorganic Chemistry,2019,vol. 58,p. 16537 - 16545

63
[ 1122-62-9 ]
[ 676-58-4 ]
[ 37988-38-8 ]
3-hydroxy-1,3-di(pyridin-2-yl)butan-1-one [ No CAS ]
meso-2,4-di(2-pyridinyl)-2,4-pentanediol [ No CAS ]
racemo-2,4-di(2-pyridynyl)-2,4-pentanediol [ No CAS ]
meso,meso-2,4,6-tri(2-pyridynyl)-2,4,6-heptanetriol [ No CAS ]
racemo,racemo-2,4,6-tri(2-pyridynyl)-2,4,6-heptanetriol [ No CAS ]
meso,racemo-2,4,6-tri(2-pyridynyl)-2,4,6-heptanetriol [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 6709 - 6719

64
[ 37988-38-8 ]
[ 15243-33-1 ]
C₂₄H₂₀N₂O₁₀Ru₃ [ No CAS ]