[ CAS No. 1570-65-6 ]

Name: 1570-65-6|2,4-Dichloro-6-methylphenol|97%
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Quality Control of [ 1570-65-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1570-65-6 ]

CAS No. :	1570-65-6	MDL No. :	MFCD00019988
Formula :	C₇H₆Cl₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WJQZZLQMLJPKQH-UHFFFAOYSA-N
M.W :	177.03	Pubchem ID :	15292
Synonyms :

Calculated chemistry of [ 1570-65-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.45
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.16
Log Po/w (XLOGP3) :	3.0
Log Po/w (WLOGP) :	3.01
Log Po/w (MLOGP) :	2.99
Log Po/w (SILICOS-IT) :	3.09
Consensus Log Po/w :	2.85

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.27
Solubility :	0.0947 mg/ml ; 0.000535 mol/l
Class :	Soluble
Log S (Ali) :	-3.09
Solubility :	0.144 mg/ml ; 0.000814 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.44
Solubility :	0.0644 mg/ml ; 0.000364 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.19

Safety of [ 1570-65-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1570-65-6 ]

* 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 [ 1570-65-6 ]
Downstream synthetic route of [ 1570-65-6 ]

[ 1570-65-6 ] Synthesis Path-Upstream 1~20

1
[ 95-48-7 ]
[ 1570-65-6 ]
[ 87-64-9 ]

Reference： [1] Journal of the American Chemical Society, 1935, vol. 57, p. 2176

2
[ 7664-93-9 ]
[ 95-48-7 ]
[ 1570-65-6 ]
[ 87-64-9 ]

Reference： [1] Journal of the American Chemical Society, 1935, vol. 57, p. 2176

3
[ 94-74-6 ]
[ 1570-65-6 ]
[ 1570-64-5 ]
[ 95-71-6 ]
[ 608-25-3 ]
[ 108372-60-7 ]
[ 553-97-9 ]
[ 95-48-7 ]
[ 488-17-5 ]
[ 87-64-9 ]

Reference： [1] Journal of Photochemistry and Photobiology A: Chemistry, 2012, vol. 228, # 1, p. 8 - 14

4
[ 95-48-7 ]
[ 1570-65-6 ]

Reference： [1] Nippon Kagaku Kaishi, 1930, vol. 51, p. 275[2] Chem.Abstr., 1932, p. 706
[3] Journal fuer Praktische Chemie (Leipzig), 1888, vol. <2> 38, p. 328
[4] Chemische Berichte, 1883, vol. 16, p. 1601
[5] Chemische Berichte, 1886, vol. 19, p. 931
[6] Gazzetta Chimica Italiana, 1899, vol. 29 II, p. 60
[7] Chemicke Listy, vol. 21, p. 159[8] Chem. Zentralbl., 1927, vol. 98, # II, p. 1344
[9] Monatshefte fuer Chemie, 1929, vol. 53/54, p. 58
[10] Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 231
[11] Patent: US5648570, 1997, A,
[12] RSC Advances, 2017, vol. 7, # 22, p. 13467 - 13472

5
[ 95-48-7 ]
[ 1570-65-6 ]
[ 87-64-9 ]

Reference： [1] Journal of the American Chemical Society, 1935, vol. 57, p. 2176

6
[ 95-48-7 ]
[ 1570-65-6 ]
[ 1570-64-5 ]

Reference： [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 6, p. 1335 - 1338

7
[ 94145-89-8 ]
[ 1570-65-6 ]

Reference： [1] Australian Journal of Chemistry, 1984, vol. 37, # 9, p. 1963 - 1968

8
[ 87-64-9 ]
[ 1570-65-6 ]

Reference： [1] Acta Chemica Scandinavica (1947-1973), 1957, vol. 11, p. 1752,1753

9
[ 94-74-6 ]
[ 1570-65-6 ]
[ 1570-64-5 ]
[ 1216257-46-3 ]
[ 95-71-6 ]
[ 553-97-9 ]
[ 95-48-7 ]

Reference： [1] Russian Journal of Applied Chemistry, 2009, vol. 82, # 3, p. 396 - 401

10
[ 7134-04-5 ]
[ 1570-65-6 ]
[ 859495-20-8 ]

Reference： [1] Journal of the Chemical Society, 1954, p. 1159

11
[ 920-39-8 ]
[ 95717-56-9 ]
[ 1570-65-6 ]
[ 60741-51-7 ]
[ 95717-63-8 ]

Reference： [1] Journal of Organic Chemistry, 1986, vol. 51, # 2, p. 174 - 179
[2] Journal of the Chemical Society, Chemical Communications, 1984, # 23, p. 1617 - 1619

12
[ 7664-93-9 ]
[ 95-48-7 ]
[ 1570-65-6 ]
[ 87-64-9 ]

Reference： [1] Journal of the American Chemical Society, 1935, vol. 57, p. 2176

13
[ 94-74-6 ]
[ 1570-65-6 ]
[ 1570-64-5 ]
[ 95-71-6 ]
[ 608-25-3 ]
[ 108372-60-7 ]
[ 553-97-9 ]
[ 95-48-7 ]
[ 488-17-5 ]
[ 87-64-9 ]

Reference： [1] Journal of Photochemistry and Photobiology A: Chemistry, 2012, vol. 228, # 1, p. 8 - 14

14
[ 56-23-5 ]
[ 7732-18-5 ]
[ 7782-50-5 ]
[ 95-48-7 ]
[ 1570-65-6 ]

Reference： [1] Promysl. org. Chim., 1937, vol. 3, p. 410[2] Chem. Zentralbl., 1938, vol. 109, # II, p. 304

15
[ 7782-50-5 ]
[ 95-48-7 ]
[ 1570-65-6 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1888, vol. <2> 38, p. 328
[2] Chemische Berichte, 1883, vol. 16, p. 1601
[3] Chemische Berichte, 1886, vol. 19, p. 931

16
[ 56-23-5 ]
[ 10026-13-8 ]
[ 7782-50-5 ]
[ 95-48-7 ]
[ 1570-65-6 ]

Reference： [1] Nippon Kagaku Kaishi, 1930, vol. 51, p. 275[2] Chem.Abstr., 1932, p. 706

17
[ 95-48-7 ]
[ 1570-65-6 ]
[ 1570-64-5 ]

Reference： [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 6, p. 1335 - 1338

18
[ 94-74-6 ]
[ 1570-65-6 ]
[ 1570-64-5 ]
[ 1216257-46-3 ]
[ 95-71-6 ]
[ 553-97-9 ]
[ 95-48-7 ]

Reference： [1] Russian Journal of Applied Chemistry, 2009, vol. 82, # 3, p. 396 - 401

19
[ 94-74-6 ]
[ 1570-65-6 ]
[ 1570-64-5 ]
[ 95-71-6 ]
[ 608-25-3 ]
[ 108372-60-7 ]
[ 553-97-9 ]
[ 95-48-7 ]
[ 488-17-5 ]
[ 87-64-9 ]

Reference： [1] Journal of Photochemistry and Photobiology A: Chemistry, 2012, vol. 228, # 1, p. 8 - 14

20
[ 1570-65-6 ]
[ 22775-37-7 ]

Reference： [1] Gazzetta Chimica Italiana, 1899, vol. 29 II, p. 60

[ 1570-65-6 ] Synthesis Path-Downstream 1~69

1
[ 141-82-2 ]
[ 1570-65-6 ]
[ 101576-57-2 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate

Reference： [1]Ziegler; Maier [Monatshefte fur Chemie, 1958, vol. 89, p. 143,152]

2
[ 1570-65-6 ]
[ 1123-64-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium dichromate; sulfuric acid
	With thallium(III) trifluoroacetate

Reference： [1]Claus; Schweitzer [Chemische Berichte, 1886, vol. 19, p. 931]
[2]McKillop,A. et al. [Tetrahedron, 1970, vol. 26, p. 4031 - 4039]

3
[ 1570-65-6 ]
[ 4592-97-6 ]

Yield	Reaction Conditions	Operation in experiment
	With chromium(VI) oxide; acetic acid
	With aqua regia

Reference： [1]Claus; Riemann [Chemische Berichte, 1883, vol. 16, p. 1601] Claus; Schweitzer [Chemische Berichte, 1886, vol. 19, p. 931]
[2]Tschulkow; Parini; Barschew [1937, vol. 3, p. 410,411][Chemisches Zentralblatt, 1938, vol. 109, # II, p. 304]

4
[ 1570-65-6 ]
[ 1760-71-0 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid; acetic acid

Reference： [1]Bures [Chemicke Listy, vol. 21, p. 161][Chemisches Zentralblatt, 1927, vol. 98, # II, p. 1344]

5
[ 1570-65-6 ]
4,6-dichloro-2-methyl-6-nitro-1-nitryloxy-cyclohexa-2,4-dienol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid

Reference： [1]Zincke [Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 231]

6
[ 1570-65-6 ]
4,6-dichloro-3-chloromethyl-2-methyl-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; formaldehyd; sulfuric acid weiteres Reagens: Methanol; Einleiten von HCl;

Reference： [1]Wegler; Regel [Makromolekulare Chemie, 1953, vol. 9, p. 1,21, 23]

7
[ 1570-65-6 ]
[ 872267-58-8 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; iron

Reference： [1]Kohn; Aron [Monatshefte fur Chemie, 1929, vol. 53/54, p. 58]

8
[ 1570-65-6 ]
dichlorophosphoric acid-(2,4-dichloro-6-methyl-phenyl ester) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With iron; trichlorophosphate
	With iron; trichlorophosphate

Reference： [1]Zenftman [1958, vol. 18, p. 361,363]
[2]Current Patent Assignee: AKZO NOBEL NV - DE809555, 1949, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.] Current Patent Assignee: HENRYK ZENFTMAN; AKZO NOBEL NV; ROY MCGILLIVRAY - GB651656, 1948, A

9
[ 1570-65-6 ]
phosphoric acid tris-(2,4-dichloro-6-methyl-phenyl ester) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrachloromethane; phosphorus pentachloride

Reference： [1]Bures [Chemicke Listy, vol. 21, p. 161][Chemisches Zentralblatt, 1927, vol. 98, # II, p. 1344]

10
[ 95-48-7 ]
[ 1570-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrachloromethane; chlorine; iron
	With chlorine
	With sulfuryl dichloride

	With chlorine at 35 - 40℃;
	With chlorine; acetic acid
	With tetrachloromethane; chlorine
	With chlorine In chlorobenzene	2.a a) a) Preparation of 2,4-dichloro-6-methyl-phenol (reaction mixture) Over a period of 2 hours, 142 g of chlorine were passed into a solution of 108 g of o-cresol in 500 ml of chlorobenzene while cooling in ice.
75 %Chromat.	With hydrogenchloride; manganese(II) sulfate; dihydrogen peroxide In water at 80℃;

Reference： [1]Tanaka; Morikawa; Sakamoto [Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1930, vol. 51, p. 275][Chem.Abstr., 1932, p. 706]
[2]Claus; Jackson [Journal fur praktische Chemie (Leipzig 1954), 1888, vol. <2> 38, p. 328] Claus; Riemann [Chemische Berichte, 1883, vol. 16, p. 1601] Claus; Schweitzer [Chemische Berichte, 1886, vol. 19, p. 931]
[3]Martini [Gazzetta Chimica Italiana, 1899, vol. 29 II, p. 60]
[4]Bures [Chemicke Listy, vol. 21, p. 159][Chemisches Zentralblatt, 1927, vol. 98, # II, p. 1344]
[5]Kohn; Aron [Monatshefte fur Chemie, 1929, vol. 53/54, p. 58]
[6]Zincke [Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 231]
[7]Current Patent Assignee: BAYER AG - US5648570, 1997, A
[8]Xin, Hongchuan; Yang, Shilei; An, Baigang; An, Zengjian [RSC Advances, 2017, vol. 7, # 22, p. 13467 - 13472]

11
[ 95-48-7 ]
[ 1570-65-6 ]
[ 87-64-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid Reaktion ueber mehrere Stufen;

Reference： [1]Huston; Neeley [Journal of the American Chemical Society, 1935, vol. 57, p. 2176]

12
[ 1570-65-6 ]
[ 96-24-2 ]
3-(2,4-dichloro-6-methyl-phenoxy)-propane-1,2-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide

Reference： [1]Ludwig et al. [Journal of the American Chemical Society, 1952, vol. 74, p. 1935,1936]

13
[ 1570-65-6 ]
[ 127-00-4 ]
[ 78021-09-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide

Reference： [1]Ludwig et al. [Journal of the American Chemical Society, 1952, vol. 74, p. 1935,1936]

14
[ 87-64-9 ]
[ 1570-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine

Reference： [1]Nord; Sjoeberg [Acta Chemica Scandinavica (1947), 1957, vol. 11, p. 1752,1753]

15
[ 1570-65-6 ]
[ 4727-41-7 ]
[ 13334-73-1 ]

Reference： [1]Monatshefte fur Chemie,1969,vol. 100,p. 1619 - 1623

16
[ 1570-65-6 ]
[ 42069-07-8 ]
[ 33348-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In benzene

Reference： [1]Current Patent Assignee: BAYER AG - DE2043204, 1971, A1 [Chem.Abstr., 1971, vol. 75, # 88306][Chem.Abstr., 1971, vol. 75, # 88306]

17
[ 1570-65-6 ]
[ 76907-92-1 ]
[ 33348-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In benzene

Reference： [1]Current Patent Assignee: BAYER AG - DE2043204, 1971, A1 [Chem.Abstr., 1971, vol. 75, # 88306][Chem.Abstr., 1971, vol. 75, # 88306]

18
[ 1570-65-6 ]
Thiophosphorochloridic acid O-ethyl ester S-(2-propoxy-ethyl) ester [ No CAS ]
[ 33348-25-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In benzene

Reference： [1]Current Patent Assignee: BAYER AG - DE2043204, 1971, A1 [Chem.Abstr., 1971, vol. 75, # 88306][Chem.Abstr., 1971, vol. 75, # 88306]

19
[ 1570-65-6 ]
Thiophosphorochloridic acid O-butyl ester S-(2-ethoxy-ethyl) ester [ No CAS ]
[ 33348-27-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In benzene

Reference： [1]Current Patent Assignee: BAYER AG - DE2043204, 1971, A1 [Chem.Abstr., 1971, vol. 75, # 88306][Chem.Abstr., 1971, vol. 75, # 88306]

20
[ 1570-65-6 ]
[ 4023-34-1 ]
[ 26065-39-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In benzene

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG; BASF SE - DE1911520, 1969, A1 [Chem.Abstr., 1970, vol. 72, # 21484][Chem.Abstr., 1970, vol. 72, # 21484]

21
[ 1570-65-6 ]
[ 7651-98-1 ]
[ 38524-84-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In benzene

Reference： [1]Current Patent Assignee: BAYER AG - US3954919, 1976, A

22
[ 1570-65-6 ]
[ 546-67-8 ]
[ 95717-56-9 ]

Yield	Reaction Conditions	Operation in experiment
41%	In acetic acid

Reference： [1]Miller, Bernard; Haggerty, John G. [Journal of Organic Chemistry, 1986, vol. 51, # 2, p. 174 - 179]

23
[ 1570-65-6 ]
[ 82592-25-4 ]

Yield	Reaction Conditions	Operation in experiment
43%	With nitric acid at 0℃; for 12h;

Reference： [1]Hartshorn, Michael P.; Ing, Huong Tuong; Richards, Kenneth E.; Thompson, Rewi S.; Vaughan, John [Australian Journal of Chemistry, 1982, vol. 35, # 1, p. 221 - 226]

24
[ 1570-65-6 ]
2,2,4,5,6-pentachloro-6-methylcyclohex-3-enone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.1 g	With hydrogenchloride; chlorine; acetic acid for 720h;

Reference： [1]Hartshorn, Michael P.; Martyn, Robert J.; Vaughan, John [Australian Journal of Chemistry, 1984, vol. 37, # 9, p. 1963 - 1968]

25
[ 1570-65-6 ]
trans-2,4,5,6,6-pentachloro-2-methylcyclohex-3-enone [ No CAS ]
cis-2,4,5,6,6-pentachloro-2-methylcyclohex-3-enone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; chlorine In acetic acid at 20℃;

Reference： [1]Hartshorn, Michael P.; Martyn, Robert J.; Vaughan, John [Australian Journal of Chemistry, 1984, vol. 37, # 4, p. 795 - 808]

26
2,2,4,5,6-pentachloro-6-methylcyclohex-3-enone [ No CAS ]
[ 1570-65-6 ]

Yield	Reaction Conditions	Operation in experiment
3.1 g	With hydrogenchloride; chlorine; acetic acid for 720h;

Reference： [1]Hartshorn, Michael P.; Martyn, Robert J.; Vaughan, John [Australian Journal of Chemistry, 1984, vol. 37, # 9, p. 1963 - 1968]

27
[ 1570-65-6 ]
[ 75-26-3 ]
[ 95717-63-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In dimethyl sulfoxide for 1h; Ambient temperature;

Reference： [1]Miller, Bernard; Haggerty, John G. [Journal of Organic Chemistry, 1986, vol. 51, # 2, p. 174 - 179]

28
[ 1570-65-6 ]
[ 22735-88-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; tetrachloromethane; chlorine

Reference： [1]Morita,E.; Dietrich,M.W. [Canadian Journal of Chemistry, 1969, vol. 47, # 11, p. 1943 - 1950]

29
[ 66074-67-7 ]
[ 1570-65-6 ]
[ 158749-52-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; triethylamine In dichloromethane for 2h; Ambient temperature;

Reference： [1]Sato, Naofumi [Tetrahedron Letters, 1996, vol. 37, # 47, p. 8519 - 8522]

Yield	Reaction Conditions	Operation in experiment
	With chlorine at 20 - 40℃;

Yield	Reaction Conditions	Operation in experiment
	With steam; sulfuric acid; sodium sulfate at 150℃;

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; chlorine Irradiation_.Einleiten auf dem Dampfbad unter der Einwirkung von Licht;

33
[ 1570-65-6 ]
[ 80526-44-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; tin(ll) chloride

Reference： [1]Zincke [Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 231]

34
[ 95-48-7 ]
[ 1570-65-6 ]
[ 1570-64-5 ]

Yield	Reaction Conditions	Operation in experiment
	With Oxone; ammonium chloride In acetonitrile at 20℃; for 24h;

Reference： [1]Narender; Mohan, K.V.V. Krishna; Srinivasu; Kulkarni; Raghavan [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 6, p. 1335 - 1338]

35
carbonic acid 2,4-dichloro-6-ethoxycarbonyloxycarbonyl-phenyl ester ethyl ester [ No CAS ]
[ 1570-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate In tetrahydrofuran at 0℃;

Reference： [1]Mazzini, Francesco; Salvadori, Piero [Synthesis, 2005, # 15, p. 2479 - 2481]

36
[ 1570-65-6 ]
2'-methyl-4', 6'-dichlorophenyl 10-carboxymethylacridinium-9-carboxylate trifluoromethane sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 80 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature 2: CH₂Cl₂ / 10 h / Ambient temperature 3: 33percent HBr/AcOH / 0.5 h / 50 °C

Reference： [1]Sato, Naofumi [Tetrahedron Letters, 1996, vol. 37, # 47, p. 8519 - 8522]

37
[ 1570-65-6 ]
Trifluoro-methanesulfonate10-benzyloxycarbonylmethyl-9-(2,4-dichloro-6-methyl-phenoxycarbonyl)-acridinium; [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 80 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature 2: CH₂Cl₂ / 10 h / Ambient temperature

Reference： [1]Sato, Naofumi [Tetrahedron Letters, 1996, vol. 37, # 47, p. 8519 - 8522]

38
[ 1570-65-6 ]
1-(4,6-dichloro-3-hydroxy-2-methyl-benzyl)-pyridinium; chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aqueous HCl; H₂SO₄; aqueous formaldehyde / weiteres Reagens: Methanol; Einleiten von HCl

Reference： [1]Wegler; Regel [Makromolekulare Chemie, 1953, vol. 9, p. 1,21, 23]

39
[ 1570-65-6 ]
[ 1760-79-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: nitric acid 2: tetrachloroethane 3: tin dichloride; concentrated hydrochloric acid 4: concentrated hydrochloric acid; glacial acetic acid; chlorine / Behandeln des Reaktionsproduktes in Alkohol mit Zinnchloruer-Loesung 5: nitric acid

Reference： [1]Zincke [Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 231]

40
[ 1570-65-6 ]
[ 320-72-9 ]

Reference： [1]Gazzetta Chimica Italiana,1899,vol. 29 II,p. 60

41
[ 1570-65-6 ]
[ 31934-88-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: nitric acid 2: tetrachloroethane 3: tin dichloride solution

Reference： [1]Zincke [Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 231]

42
[ 1570-65-6 ]
[ 22775-37-7 ]

Reference： [1]Gazzetta Chimica Italiana,1899,vol. 29 II,p. 60

43
[ 1570-65-6 ]
[ 1760-78-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: nitric acid 2: tetrachloroethane 3: tin dichloride; concentrated hydrochloric acid 4: concentrated hydrochloric acid; glacial acetic acid; chlorine / Behandeln des Reaktionsproduktes in Alkohol mit Zinnchloruer-Loesung 5: concentrated sulfuric acid

Reference： [1]Zincke [Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 231]

44
[ 1570-65-6 ]
[ 859180-25-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: iron powder; bromine 2: zinc dust; glacial acetic acid

Reference： [1]Kohn; Aron [Monatshefte fur Chemie, 1929, vol. 53/54, p. 58]

45
[ 1570-65-6 ]
3-bromo-4,6-dichloro-2-methyl-anisole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: iron powder; bromine 2: zinc dust; glacial acetic acid 3: NaOH-solution

Reference： [1]Kohn; Aron [Monatshefte fur Chemie, 1929, vol. 53/54, p. 58]

46
[ 1570-65-6 ]
3,5-dibromo-2,4-dichloro-6-methyl-anisole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: iron powder; bromine 2: KOH-solution

Reference： [1]Kohn; Aron [Monatshefte fur Chemie, 1929, vol. 53/54, p. 58]

47
[ 913298-43-8 ]
[ 1570-65-6 ]
2-(2,4-dichloro-6-methylphenoxy)-7-(3,5-diethyl-1H-pyrazol-1-yl)-1-methyl-1H-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 132h;	162 A suspension of 2-chloro-7- (3, 5-diethyl-lH-pyrazol-l- yl)-l-methyl-li-benzimidazole (92 mg, 0.318 mmol) , 2,4- dichloro-6-methylphenol (114 mg, 0.643 mmol), potassium carbonate (89 mg, 0.643 mmol) in N,_V-dimethylformainide (1.5 ml) was stirred at 90 0C for 5.5 days (2, 4-dichloro-6- methylphenol and potassium carbonate were added in three equal portions each over 5.5 days) . After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 10-25% ethyl acetate/n-hexane gradient mixture to give 107 mg (0.249 mmol, 78.3%) of the title compound as an oil. The oil was crystallized from hexane to give 70 mg (51%) as a pale yellow crystal, mp: 115-119 0C1H NMR (CDCl3) . δ: 1.19 (3H, t, J = 7.5 Hz), 1.32 (3H, t, J = 7.5 Hz), 2.26 (3H, s) , 2.50 (2H, q, J = 7.5 Hz), 2.72 (2H, EPO q, J = 7.5 Hz), 3.23 (3H, s) , 6.10 (IH, s) , 7.09-7.19 (3H, m) , 7.31 (IH, d, J = 2.4 Hz), 7.57 (IH, d, J = 6.9 Hz). MS Calcd. : 428; Found: 429 (M+H) , 431.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2006/116412, 2006, A2 Location in patent: Page/Page column 236-238

48
[ 913298-61-0 ]
[ 1570-65-6 ]
4-chloro-2-(2,4-dichloro-6-methylphenoxy)-1-methyl-7-(pentan-3-yl)-1H-benzo[d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 34h;	4.2.40. 4-Chloro-2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole 24d General procedure: A solution of compound 23b (5.5 g, 20.2 mmol), 2,4-dichloro-6-methylphenol (10 g, 56.5 mmol) and potassium carbonate (8.4 g,60.8 mmol) in DMF (55 mL) was heated at 100 C for 9 h. To the mixture was added 2,4-dichloro-6-methylphenol (5 g, 28.3 mmol)and potassium carbonate (4.2 g, 30.4 mmol) and heated at 100 Cfor 16 h. Additional 2,4-dichloro-6-methylphenol (5 g, 28.3 mmol)and potassium carbonate (4.2 g, 30.4 mmol) were added andheated at 100 C for 9 h. After cooling, the mixture was diluted with H2O and extracted with EtOAc. The extract was washed with brine, dried and concentrated in vacuo. The residue was purified by column chromatography on NH silica gel eluting with a 12.5%EtOAc/n-hexane. The resulting solids were recrystallized from a10% EtOAc/n-hexane to give the title compound (5.3 g, 64%) as acolorless crystal. mp 155-157 C. MS Calcd.: 410; Found: 411 (M+H). 1H NMR (CDCl3) d 0.86 (6H, t, J = 7.2 Hz), 1.64-1.86 (4H, m),2.31 (3H, s), 3.17-3.28 (1H, m), 3.99 (3H, s), 6.93 (1H, d,J = 8.4 Hz), 7.14 (1H, d, J = 8.4 Hz), 7.20 (1H, d, J = 2.4 Hz), 7.31(1H, d, J = 2.4 Hz). 13C NMR (151 MHz, DMSO-d6) d 154.6, 146.3,136.5, 134.8, 133.5, 130.6, 130.0, 128.5, 127.4, 127.1, 121.6,120.1, 118.8, 39.8, 32.1, 28.2, 15.9, 11.6. Anal. Calcd for C20H21N2-OCl3: C, 58.34; H, 5.14; N, 6.80. Found: C, 58.35; H, 5.13; N, 6.86
64%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 34h;	97 A solution of 2, 4-dichloro-7- (1-ethylpropyl) -1-methyl- IH-benzimidazole (5.5 g, 20.2 rranol), 2, 4-dichloro-6- methylphenol (1Og, 56.5 mmol) and potassium carbonate (8.4g, 60.8 mmol) in N, I7-dimethylformamide (55 inL) was heated at 100 0C for 9 h. To the mixture was added 2, 4-dichloro-6- methylphenol (5g, 28.3 mmol) and potassium carbonate (4.2g, 30.4 mmol) and heated at 100 0C for 16 h. Additional 2,4- dichloro-6-methylphenol (5g, 28.3 mmol) and potassium carbonate (4.2g, 30.4 mmol) were added and heated at 100 0C for 9 h. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, filtered and EPO concentrated in vacuo. The residue was purified by column chromatography on NH silica gel eluting with a 12.5% ethyl acetate/n-hexane . The resulting solids were recrystalized from a 10% ethyl acetate/n-hexane to give 5.3 g (64%) of the title compound as a colorless crystal, mp 155-157 0C.1H NMR (CDCl3) δ 0.86 (t, J =7.2 Hz, 6H), 1.64-1.86 (m, 4H), 2.31 (s, 3H), 3.17-3.28 (m, IH), 3.99 (s, 3H), 6.93 (d, J = 8.4 Hz, IH), 7.14 (d, J = 8.4 Hz, IH), 7.20 (d, J= 2.4 Hz, IH), 7.31 (d, J= 2.4 Hz, IH).MS Calcd. : 410; Found: 411 (M+H) .
5.57 g	With potassium phosphate In dimethyl sulfoxide at 105℃; for 12h;

Reference： [1]Mochizuki, Michiyo; Kojima, Takuto; Kobayashi, Katsumi; Kotani, Etsuo; Ishichi, Yuji; Kanzaki, Naoyuki; Nakagawa, Hideyuki; Okuda, Teruaki; Kosugi, Yohei; Yano, Takahiko; Sako, Yuu; Tanaka, Maiko; Aso, Kazuyoshi [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 5, p. 1556 - 1570]
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2006/116412, 2006, A2 Location in patent: Page/Page column 155; 156
[3]Sawai, Yasuhiro; Yabe, Osamu; Nakaoka, Keiichiro; Ikemoto, Tomomi [Organic Process Research and Development, 2017, vol. 21, # 2, p. 222 - 230]

49
[ 913299-00-0 ]
[ 1570-65-6 ]
2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 12h;	145 A mixture of 2, 4-dichloro-7- (1-ethylpropyl) -1-methyl- li-benzimidazole (200 mg, 0.750 mmol) , 2, 4-dichloro-6- methylphenol (398 mg, 2.25 mmol), potassium carbonate (311 mg, 2.25 mmol) and l-methyl-2-pyrrolidone (0.5 ml) was stirred at 120 0C for 12 h under nitrogen atmosphere. The mixture was diluted with water, extracted with ethyl acetate, and washed with brine. The organic layer was dried over magnesium sulfate, and concentrated in vacuo.The residue was purified by chromatography on silica gel with a 2-30% ethyl acetate/n-hexane gradient mixture and crystallized from methanol to afford the title compound as colorless crystals (109 mg, 36%) . EPO mp 130-131 0C.1H NMR (CDCl3) δ 0.86 (t, J = 7.5 Hz, 6H), 1.60-1.85 (m,4H), 2.30 (s, 3H), 3.15-3.25 (m, IH), 3.89 (s, 3H), 3.97 (s,3H), 6.64 (d, J = 8.4 Hz, IH), 6.92 (d, J = 8.4 Hz, IH),7.15 (d, J= 1.8 Hz, IH), 7.25 (d, J = 1.8 Hz, IH).MS Calcd. : 406; Found: 407 (M+H) , 409.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2006/116412, 2006, A2 Location in patent: Page/Page column 205; 206

50
methyl 2-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate [ No CAS ]
[ 1570-65-6 ]
methyl 2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 5h;	153 A mixture of methyl 2-chloro-7- (1-ethylpropyl) -1- methyl-lH-benzimidazole-4-carboxylate (1.15 g, 3.90 mmol) , 4, 6-dichloro-o-cresol (2.07 g, 11.70 mmol), potassium carbonate (2.16 g, 15.60 mmol) and WVV-dimethylformamide (15 ml) was heated at 110 0C for 5 h. The residue was diluted with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on alumina with a 15% ethyl acetate/n-hexane to give 1.41 g (3.24 mmol, 83%) of the title compound as a white powder, mp 177-178 0C. 1H NMR (CDCl3) δ 0.86 (t, J = 7.44 Hz, 6H), 1.65-1.92 (m, 4H), 2.36 (s, 3H), 3.25-3.39 (m, IH), 3.84 (s, 3H), 4.03 (s, 3H) 7.06 (d, J = 8.29 Hz, IH), 7.21 (d, J = 1.88 Hz, IH), 7.30 (d, J= 2.64 Hz, IH), 7.79 (d, J= 8.29 Hz, IH). MS: Calcd. : 435; Found: 436 (M+H) .

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2006/116412, 2006, A2 Location in patent: Page/Page column 218

51
[ 913299-86-2 ]
[ 1570-65-6 ]
2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 48h;	160 A mixture of 2-chloro-7- (1-ethylpropyl) -l-methyl-4-(trifluoromethyl) -lif-benzimidazole (304 mg, 1.00 mmol) ,4, 6-dichloro-o-cresol (531 mgr 3.00 mmol), potassium carbonate (553 mg,4.0 mmol) and _V,N-dimethylformamide (5 ml) was heated at 110 0C for 48 h. Aqueous saturated sodium bicarbonate was added to the residue and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with a 10% ethyl acetate/n-hexane and recrystallization from diisopropylether/n-hexane to give 290 mg (0.65 mmol, 65%) of the title compound as a white powder, mp. 149-151 0C 1H NMR (CDCl3) δ 0.87 (t, J = 7.35 Hz, 6H), 1.66-1.91 (m, 4H), 2.31 (s, 3H), 3.24-3.37 (m, IH), 4.02 (s, 3H), 7.05 (d, J = 8.10 Hz, IH), 7.21 (d, J = 1.88 Hz, IH), 7.31 (d, J = 2.45 Hz, IH), 7.39 (d, J= 8.10 Hz, IH). MS Calcd. : 445; Found: 446 (M+H) .

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2006/116412, 2006, A2 Location in patent: Page/Page column 234; 235

52
[ 876-08-4 ]
[ 1570-65-6 ]
4-Chloromethylbenzoicacid-(2,4-dichloro-6-methylphenyl)-ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In 5,5-dimethyl-1,3-cyclohexadiene; nitrogen; Petroleum ether	12 4-Chloromethylbenzoicacid-(2,4-dichloro-6-methylphenyl) ester STR9 EXAMPLE 12 4-Chloromethylbenzoicacid-(2,4-dichloro-6-methylphenyl) ester STR9 88.5 g (0.5 mole) of 2,4-dichloro-6-methylphenol, 180 ml of dry xylene, 95 g (0.5 mole) of p-chloromethylbenzoyl chloride and 0.5 ml of pyridine were refluxed for 24 hours in a weak current of nitrogen with the exclusion of moisture. After cooling, the slightly turbid (pyridine hydrochloride), orange-colored solution was filtered free of a small amount of a blackish brown resin, and the filtrate was freed of xylene at diminished pressure. The residue (165 g=100%) crystallized after two days of standing to a light brown crystal mass, which was triturated in 200 ml of ice-cold petroleum ether and suction filtered. After drying, nearly colorless crystals were obtained with a melting point of 71°-73° C. Recrystallization from petroleum ether (1:10) yielded white needles melting at 74°-75° C.; no change in the melting point was brought about by repeated recrystallization. Elemental analysis: C15 H11 Cl3 O2 (Mol. wt. 329.62). Calculated: C 54.66%; H 3.36%; Cl 32.27%; O 9.71%. Found: C 54.71%; H 3.28%; Cl 32.11%; O 9.89%.

Reference： [1]Current Patent Assignee: ALBEMARLE CORP - US4260803, 1981, A

53
[ 1022250-90-3 ]
[ 1570-65-6 ]
[ 1022249-72-4 ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: 2-[4-bromo-2-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]-N,N-dimethylethanamine; 4,6-dichloro-2-methylphenol With potassium carbonate In 1-methyl-pyrrolidin-2-one at 110℃; for 0.5h; Stage #2: With sodium hydrogencarbonate In 1-methyl-pyrrolidin-2-one; water	63 To a solution of 2- [4-bromo-2-chloro-7- ( 1- ethylpropyl) -ltf-benzimidazol-1-yl] -N, N-dimethylethanamine (7.4 mg, 0.0199 mmol) in l-methyl-2-pyrrolidone (0.5 mL) were added 2, 4-dichloro-6-methylphenol (11 mg, 0.060 mmol) and potassium carbonate (8.2 mg, 0.0560 mmol), and the mixture was stirred at 1100C for 30 min. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate (X2). The combined organic layer was washed with EPO brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC eluting with a 25% ethyl acetate/n-hexane gradient mixture to give the title compound (7.0 mg, 0.0136 mmol, 69%) as an oil.1H NMR (CDCl3) δ 0.90 (t, J = 7.2 Hz, 6H), 1.65-1.87 (m, 4H), 2.30 (s, 3H), 2.37 (s, 6H), 2.79 (t, J = 7.8 Hz, 2H), 3.04-3.13 (m, IH), 4.47 (t, J = 7.8 Hz, 2H), 6.89 (d, J = 8.4 Hz, IH), 7.20-7.33 (m, 3H). MS Calcd.: 511, MS Found: 512 (M+H) .

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/51533, 2008, A2 Location in patent: Page/Page column 164-165

54
[ 1022251-06-4 ]
[ 1570-65-6 ]
[ 1022251-63-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate In 1-methyl-pyrrolidin-2-one at 110℃; for 96h;	64.i To a solution of 2, 7-dichloro-4- (1-ethylpropyl) -1- (4- methoxybenzyl) -IH-benzimidazole (205 mg, 0.543 mmol) in 1- methyl-2-pyrrolidone (2.0 mL, 20.8 mmol) were added 2,4- dichloro-6-methylphenol (289 mg, 1.63 mmol) and potassium carbonate (225 mg, 1.630 mmol), and the mixture was stirred at 100°C for 4 days. The reaction mixture was diluted with water and extracted with ethyl acetate (X2) . The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-3% ethyl acetate/n-hexane gradient mixture. The fractions containing the title compound were concentrated in vacuo, and the residual solid was washed with water. The solid was recrystallized from n-hexane to give the EPO title compound (261 mg, 0.504 mmol, 93%) as a colorless solid .1H NMR (CDCl3) δ 0.69 (t, J = 7.2 Hz, 6H), 1.54-1.70 (m, 4H), 2.08 (s, 3H), 2.93-3.04 (m, IH), 3.79 (s, 3H), 5.69 (s, 2H), 6.83-6.87 (m, 3H), 7.05 (d, J = 8.1 Hz, IH), 7.16 (d, J = 1.8 Hz, IH), 7.24-7.31 (m, 3H). MS Calcd.: 516, MS Found: 517 (M+H) .

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/51533, 2008, A2 Location in patent: Page/Page column 165-166

55
[ 1022251-19-9 ]
[ 1570-65-6 ]
[ 1022249-87-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 20h;	70 A mixture of 4-bromo-2-chloro-7- (1-ethylpropyl) -1-methyl- lH-benzimidazole (4.15 g, 13.1 mmol) , 2, 4-dichloro-6- methylphenol (6.97 g, 39.4 mmol), potassium carbonate (5.45 g, 39.4 mmol) and N, N-dimethylformamide (10 mL) was stirred at 120°C for 20 hr. The mixture was diluted with water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 0-10% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give a solid, which was recrystallized from ethyl acetate/n-hexane to give the title compound as colorless crystals (4.48 g, 9.82 mmol, 75%) . mp 146-147°C.1H NMR (CDCl3) δ 0.86 (t, J = 7.5 Hz, 6H), 1.68-1.79 (m, 4H), 2.31 (s, 3H), 3.20-3.24 (m, IH), 3.98 (s, 3H), 6.88 (d, J = 8.7 Hz, IH), 7.20 (d, J = 2.4 Hz, IH), 7.26 (d, J = 8.7 Hz, IH), 7.30 (d, J= 2.4 Hz, IH).MS Calcd.: 454; MS Found: 455 (M+H) .

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/51533, 2008, A2 Location in patent: Page/Page column 170-171

56
[ 1022251-20-2 ]
[ 1570-65-6 ]
[ 1022249-92-8 ]

Yield	Reaction Conditions	Operation in experiment
11%	With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 19h;	73 A mixture of 2-chloro-4-ethoxy-7- ( 1-ethylpropyl) -1-methyl- ltf-benzimidazole (609 mg, 2.16 irunol), 2, 4-dichloro-6- methylphenol (1.15 g, 6.50 mmol), potassium carbonate (898 mg, 6.50 mmol) and N, N-dimethylformamide (2.0 itiL) was stirred at 1200C for 19 hr . The mixture was diluted with water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 0-10% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/n- hexane to give the title compound as colorless crystals (97.1 mg, 0.230 mmol, 11%). mp 116-1170C.1H NMR (CDCl3) δ 0.86 (t, J = 7.5 Hz, 6H), 1.39 (t, J = 6.9 Hz, 3H), 1.60-1.78 (m, 4H), 2.30 (s, 3H), 3.16-3.20 (m, IH), 3.96 (s, 3H), 4.19 (q, J = 6.9 Hz, 2H), 6.63 (d, J = 8.4 Hz, IH), 6.89 (d, J = 8.4 Hz, IH), 7.17 (d, J = 2.4 Hz, IH), 7.27 (d, J = 2.4 Hz, IH) . MS Calcd.: 420; MS Found: 421 (M+H) .

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/51533, 2008, A2 Location in patent: Page/Page column 174

57
[ 1022251-29-1 ]
[ 1570-65-6 ]
[ 1022250-28-7 ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 13h;	92 mixture of 1- (2, 4-dichloro-l-methyl-lH-benzimidazol- 7-yl) propan-1-one (3.51 g, 13.7 ϖunol), 2, 4-dichloro-6- methylphenol (7.25 g, 40.9 mmol) , potassium carbonate (5.65 g, 40.9 mmol) and N, N-dimethylformamide (10 mL) was stirred at 1100C for 13 hr. The mixture was diluted with water and extracted with ethyl acetate. The extract was washed with IN aqueous sodium hydroxide, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with ethyl acetate to give the title compound as a colorless powder (3.09 mg, 7.77 mmol, 57%) .1H NMR (CDCl3) 8 1.47 (t, J = 7.2 Hz, 3H), 2.25 (s, 3H), 3.13 (q, J = 7.2 Hz, 2H), 3.72 (s, 3H), 7.32 (d, J = 8.1 Hz,IH) , 7.55 (d, J = 2.7 Hz, IH: 7.66 (d, J = 8.1 Hz, IH) ,7.69 (d, J = 2.7 Hz, IH) .MS Calcd.: 396; MS Found: 397 (M+H) .

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/51533, 2008, A2 Location in patent: Page/Page column 191-192

58
[ 1022251-70-2 ]
[ 1570-65-6 ]
[ 1022250-26-5 ]

Yield	Reaction Conditions	Operation in experiment
28%	With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 96h;	91 A mixture of 2-chloro-7- (1-ethylpropyl) -1-methyl-IH- benzimidazole (382 mg, 1.61 mmol), 2, 4-dichloro-6- methylphenol (852 mg, 4.84 mmol), potassium carbonate (669 mg, 4.84 mmol) and N, N-dimethylformamide (0.5 itiL) was stirred at 1100C for 4 days. After cooling, the reaction mixture was neutralized with aqueous saturated sodium hydrogen carbonate and extracted with ethyl acetate (X3) . The combined organic layer was washed with IN aqueous sodium hydroxide (X2), washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by basic silica gel column chromatography eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The resulting solid was recrystallized from ethyl acetate/n-hexane to give the title compound as a colorless powder (169.9 mg, 0.450 mmol, 28%). mp 91-92°C.1H NMR (CDCl3) δ: 0.88 (t, J = 7.5 Hz, 6H), 1.72-1.84 (m, 4H), 2.30 (s, 3H), 3.23-3.28 (m, IH), 4.00 (s, 3H), 7.00- 7.20 (m, 3H), 7.31-7.37 (m, 2H). MS Calcd.: 376, MS Found: 377 (M+H) .

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/51533, 2008, A2 Location in patent: Page/Page column 190-191

59
[ 1064653-97-9 ]
[ 1570-65-6 ]
[ 1064654-34-7 ]
[ 1064654-42-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 55% 2: 18%	With potassium carbonate In acetonitrile at 40 - 50℃;

Reference： [1]Liu, Ming-Guo; Hu, Yang-Gen; Ding, Ming-Wu [Tetrahedron, 2008, vol. 64, # 38, p. 9052 - 9059]

60
[ 1570-65-6 ]
4-(5-chloro-6-fluoropyridin-3-YL)-3-methoxy-N-(methylsulfonyl)benzamide [ No CAS ]
4-(5-chloro-6-(2,4-dichloro-6-methylphenoxy)-3-pyridinyl)-3-methoxy-N-( methylsulfonyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51.6 mg	With caesium carbonate In dimethyl sulfoxide at 90℃; for 40h;	578 EXAMPLE 578: 4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY)-PYRIDIN-3- YL)-3-METHOXY-N-(METHYLSULFONYL)BENZAMIDE EXAMPLE 578: 4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY)-PYRIDIN-3- YL)-3-METHOXY-N-(METHYLSULFONYL)BENZAMIDE[00226] 2,4-dichloro-6-methylphenol (80 mg, 0.452 mmol), cesium carbonate (276 mg, 0.847 mmol), and 4-(5-chloro-6-fluoropyridin-3-yl)-3-methoxy-N-(methylsulfonyl)benzamide (INTERMEDIATE L, see above Method XI, 101 mg, 0.282 mmol) were combined in a 2 dram resealable reaction vessel and DMSO (2 mL) was added. The vial was sealed and heated at 90 °C for 40 h. The crude reaction mixture was then filtered through a frit and washed with DCM, then MeOH. After concentration, the crude residue was purified using preparative reverse phase HPLC (0.1% NH4OH in water/acetonitrile; Flow rate: 40 ml/min; Gradient: 10 min 20- 50% NH3) to afford 4-(5-chloro-6-(2,4-dichloro-6-methylphenoxy)pyridin-3-yl)-3-methoxy-N- (methylsulfonyl)benzamide (51.6 mg). LC-MS m/z (ESI, negative ion) 514.0. 1H NMR (500 MHz, DMSO-de) δ 8.24-8.28 (m, 1H), 8.15-8.19 (m, 1H), 7.66-7.70 (m, 1H), 7.59-7.65 (m, 2H), 7.46-7.50 (m, 1H), 7.38-7.43 (m, 1H), 3.84 (s, 3H), 3.01 (s, 3H), 2.15 (s, 3H).

Reference： [1]Current Patent Assignee: AMGEN INC - WO2015/51043, 2015, A1 Location in patent: Paragraph 00226

61
[ 1570-65-6 ]
5-chloro-4-(5-chloro-6-fluoropyridin-3-yl)-2-fluoro-N-(methylsulfonyl)benzamide [ No CAS ]
5-chloro-4-(5-chloro-6-(2,4-dichloro-6-methylphenoxy)-3-pyridinyl)-2-fluoro-N-(methylsulfonyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With caesium carbonate In dimethyl sulfoxide at 90℃;	598 EXAMPLE 598: 5-CHLORO-4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY) PYRIDIN-3-YL)-2-FLUORO-N-(METHYLSULFONYL)BENZAMIDE EXAMPLE 598: 5-CHLORO-4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY) PYRIDIN-3-YL)-2-FLUORO-N-(METHYLSULFONYL)BENZAMIDE[00266] To a vial charged with 5-chloro-4-(5-chloro-6-fluoropyridin-3-yl)-2-fluoro-N- (methylsulfonyl)benzamide (65 mg, 0.171 mmol) and CS2CO3(167 mg, 0.512 mmol) was added 2,4-dichloro-6-methylphenol (0.239 mmol, 1.4 eq, Frontier Scientific) and DMSO (0.3 M). The resulting suspension was heated with shaking at 90 °C overnight. The resulting suspension was filtered through a frit, rinsing with isopropanol. The isopropanol was removed in-vacuo and the crude material purified Waters-Xbridge C18, 19 x 100 mm, 10 μιη column with a gradient 5-95% acetonitrile and water with 0.1 % NH4OH to afford 5-chloro-4-(5- chloro-6-(2,4-dichloro-6-methylphenoxy)pyridin-3-yl)-2-fluoro-n-(methylsulfonyl)benzamide (49 mg, 37%). LC-MS m/z (ESI, negative ion) 536.8. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.15 (s, 3 H) 2.89 (s, 3 H) 7.40 (d, J=10.51 Hz, 1 H) 7.45 - 7.54 (m, 1 H) 7.63 (d, J=2.14 Hz, 1 H) 7.81 (d, J=6.68 Hz, 1 H) 8.15 (d, J=2.01 Hz, 1 H) 8.30 (d, J=2.01 Hz, 1 H).

Reference： [1]Current Patent Assignee: AMGEN INC - WO2015/51043, 2015, A1 Location in patent: Paragraph 00266

62
[ 1570-65-6 ]
4-(5-bromo-6-fluoropyridin-3-yl)-2,5-difluoro-N-(methylsulfonyl)benzamide [ No CAS ]
4-(5-bromo-6-(2,4-dichloro-6-methylphenoxy)-3-pyridinyl)-2,5-difluoro-N-( methylsulfonyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16 mg	With caesium carbonate In dimethyl sulfoxide at 90℃; for 40h;	787.1 STEP 1 : 4-(5-BROMO-6-(2,4-DICHLORO-6-METHYLPHENOXY)PYRIDIN-3-YL)-2,5- DIFLUORO-N-(METHYLSULFONYL)BENZAMIDE STEP 1 : 4-(5-BROMO-6-(2,4-DICHLORO-6-METHYLPHENOXY)PYRIDIN-3-YL)-2,5- DIFLUORO-N-(METHYLSULFONYL)BENZAMIDE[00321 ] A 2 dram reasealable vial was charged with 2,4-dichloro-6-methylphenol (80 mg, 0.452 mmol), cesium carbonate (276 mg, 0.847 mmol), and 4-(5-bromo-6-fluoropyridin-3- yl)-2,5-difluoro-N-(methylsulfonyl)benzamide (116 mg, 0.282 mmol, Intermediate U) and DMSO (2 mL) was added. The vial was sealed and heated at 90 °C for 40 h. The reaction mixture was then filtered through a frit, washing with DCM and MeOH. After concentration, the crude residue was purified using preparative reverse phase LCMS (0.1% NH4OH in water/acetonitrile; Flow rate: 40 ml/min; Gradient: 10 min 20-50% NH3) to afford 4-(5-bromo- 6-(2,4-dichloro-6-methylphenoxy)pyridin-3-yl)-2,5-difluoro-N-(methylsulfonyl)benzamide (16 mg). LC-MS m/z (ESI, negative ion) 564.8.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2015/51043, 2015, A1 Location in patent: Paragraph 00321

63
[ 1570-65-6 ]
4-(5-chloro-6-fluoropyridin-3-yl)-3-methyl-N-(methylsulfonyl)benzamide [ No CAS ]
4-(5-chloro-6-(2,4-dichloro-6-methylphenoxy)-3-pyridinyl)-3-methyl-N-(methylsulfonyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In dimethyl sulfoxide at 90℃; for 40h;	775.3 STEP 3 : 4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY)-3-PYRIDINYL)-3- METHYL-N-(METHYLSULFONYL)BENZAMIDE STEP 3 : 4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY)-3-PYRIDINYL)-3- METHYL-N-(METHYLSULFONYL)BENZAMIDE[00299] A 2 dram reasealable vial was charged with 2,4-dichloro-6-methylphenol (80 mg, 0.452 mmol), cesium carbonate (276 mg, 0.847 mmol), and 4-(5-chloro-6-fluoropyridin-3- yl)-3-methyl-N-(methylsulfonyl)benzamide (97 mg, 0.282 mmol, Intermediate AD) and DMSO (2 mL) was added. The vial was sealed and heated at 90 °C for 40 h. The reaction mixture was then filtered through a frit, washing with DCM and MeOH. After concentration, the crude residue was purified using preparative reverse phase LCMS (0.1% NH4OH inwater/acetonitrile; Flow rate: 40 ml/min; Gradient: 10 min 20-50% NH3) to afford 4-(5-chloro- 6-(2,4-dichloro-6-methylphenoxy)-3-pyridinyl)-3-methyl-N-(methylsulfonyl)benzamide. MS m/z (ESI, negative ion) 498.8.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2015/51043, 2015, A1 Location in patent: Paragraph 00299

64
[ 1570-65-6 ]
3-chloro-4-(5-chloro-6-fluoropyridin-3-yl)-N-(methylsulfonyl)benzamide [ No CAS ]
3-chloro-4-(5-chloro-6-(2,4-dichloro-6-methylphenoxy)-3-pyridinyl)-N-(methylsulfonyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In dimethyl sulfoxide at 90℃; for 4h;	776.3 STEP 3 : 3-CHLORO-4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY)-3- PYRIDINYL)-N-(METHYLSULFONYL)BENZAMIDE STEP 3 : 3-CHLORO-4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY)-3- PYRIDINYL)-N-(METHYLSULFONYL)BENZAMIDE[00302] A 2 dram reasealable vial was charged with 2,4-dichloro-6-methylphenol (80 mg, 0.452 mmol), cesium carbonate (276 mg, 0.847 mmol), and 3-chloro-4-(5-chloro-6- fluoropyridin-3-yl)-N-(methylsulfonyl)benzamide (103 mg, 0.282 mmol, Intermediate AE) and DMSO (2 mL) was added. The vial was sealed and heated at 90 °C for 40 h. The reaction mixture was then filtered through a frit, washing with DCM and MeOH. After concentration, the crude residue was purified using preparative reverse phase LCMS (0.1 %> NH4OH in water/acetonitrile; Flow rate: 40 ml/min; Gradient: 10 min 20-50% NH3) to afford 3-chloro-4- (5-chloro-6-(2,4-dichloro-6-methylphenoxy)-3-pyridinyl)-N-(methylsulfonyl)benzamide. MS m/z (ESI, negative ion) 518.8/520.8.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2015/51043, 2015, A1 Location in patent: Paragraph 00302

65
[ 1570-65-6 ]
4-(5-chloro-6-fluoropyridin-3-yl)-5-(difluoromethoxy)-2-fluoro-N-(methylsulfonyl)benzamide [ No CAS ]
4-(5-chloro-6-(2,4-dichloro-6-methylphenoxy)-3-pyridinyl)-5-(difluoromethoxy)-2-fluoro-N-(methylsulfonyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.6 mg	With caesium carbonate In dimethyl sulfoxide at 150℃; for 2h; Microwave irradiation;	782 EXAMPLE 782: 4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY)-3-PYRIDINYL)-5-(DIFLUOROMETHOXY)-2-FLUORO-N-(METHYLSULFONYL)BENZAMIDE EXAMPLE 782: 4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY)-3-PYRIDINYL)-5-(DIFLUOROMETHOXY)-2-FLUORO-N-(METHYLSULFONYL)BENZAMIDE[00314] To a microwave vessel charged with 2,4-dichloro-6-methylphenol (103 mg, 0.581 mmol) was added 4-(5-chloro-6-fluoropyridin-3-yl)-5-(difluoromethoxy)-2-fluoro-N- (methylsulfonyl)-benzamide (INTERMEDIATE AG) (0.080 g, 0.194 mmol) and DMSO (2 mL). Then cesium carbonate (0.253 g, 0.775 mmol) was added. The tube was sealed and heated at 150 °C in the microwave for 2 h. The crude reaction mixture was then filtered through a frit and washed with DCM then MeOH. After concentration, the crude residue was purified using preparative reverse phase LCMS (0.1% NH4OH in water/acetonitrile; Flow rate: 40 ml/min; Gradient: 10 min 20-50% NH3) to afford 4-(5-chloro-6-(2,4-dichloro-6- methylphenoxy)-3-pyridinyl)-5-(difluoromethoxy)-2-fluoro-N-(methylsulfonyl)benzamide (50.6 mg). LC-MS m/z (ESI, positive ion) 569.0. 1H NMR (500 MHz, DMSO-d6) δ 8.29 (d, J=2.01 Hz, 1H), 8.17 (d, J=1.95 Hz, 1H), 7.63 (d, J=2.14 Hz, 1H), 7.58 (d, J=6.10 Hz, 1H), 7.49 (d, J=1.82 Hz, 1H), 7.44 (d, J=10.51 Hz, 1H), 7.01-7.33 (m, 1H), 2.93 (s, 3H), 2.14 (s, 3H).

Reference： [1]Current Patent Assignee: AMGEN INC - WO2015/51043, 2015, A1 Location in patent: Paragraph 00314

66
[ 1570-65-6 ]
3-bromo-4-(5-chloro-6-fluoropyridin-3-yl)-N-(methylsulfonyl)benzamide [ No CAS ]
3-bromo-4-(5-chloro-6-(2,4-dichloro-6-methylphenoxy)-3-pyridinyl)-N-(methylsulfonyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88 mg	With caesium carbonate In dimethyl sulfoxide at 90℃; for 40h;	794.3 STEP 3: 3-BROMO-4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY)-3- PYRIDINYL)-N-(METHYLSULFONYL)BENZAMIDE STEP 3: 3-BROMO-4-(5-CHLORO-6-(2,4-DICHLORO-6-METHYLPHENOXY)-3- PYRIDINYL)-N-(METHYLSULFONYL)BENZAMIDE[00340] A 2 dram reasealable vial was charged with 2,4-dichloro-6-methylphenol (80 mg, 0.452 mmol), cesium carbonate (276 mg, 0.847 mmol), and 3-bromo-4-(5-chloro-6- fluoropyridin-3-yl)-N-(methylsulfonyl)benzamide (115 mg, 0.282 mmol, Intermediate AN) and DMSO (2 mL) was added. The vial was sealed and heated at 90 °C for 40 h. The reaction mixture was then filtered through a frit, washing with DCM and MeOH. After concentration, the crude residue was purified using preparative reverse phase LCMS (0.1 % NH4OH in water/acetonitrile; Flow rate: 40 ml/min; Gradient: 10 min 20-50% NH3) to afford 3-bromo-4- (5-chloro-6-(2,4-dichloro-6-methylphenoxy)-3-pyridinyl)-N-(methylsulfonyl)benzamide (88 mg). MS m/z (ESI, negative ion) 563.0.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2015/51043, 2015, A1 Location in patent: Paragraph 00340

67
[ 1570-65-6 ]
sodium bis-(2,6-dimethylphenyl)phosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: trichlorophosphate; pyridine / benzene / 10 h / Reflux; Inert atmosphere 1.2: 0.25 h / Inert atmosphere; Reflux 2.1: sodium / methanol

Reference： [1]Minyaev, Mikhail E.; Korchagina, Sof′ya A.; Tavtorkin, Alexander N.; Kostitsyna, Nataliya N.; Churakov, Andrei V.; Nifant′ev, Ilya E.; Nifantev, Ilya E. [Structural Chemistry, 2018, vol. 29, # 5, p. 1475 - 1487]

68
[ 1570-65-6 ]
potassium bis(2,4-dichloro-6-methylphenyl)phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: trichlorophosphate; pyridine / benzene / 10 h / Reflux; Inert atmosphere 1.2: 0.25 h / Inert atmosphere; Reflux 2.1: potassium hydroxide / water; methanol / pH 7

69
[ 1570-65-6 ]
bis(2,4-dichloro-6-methylphenyl)phosphoric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 4,6-dichloro-2-methylphenol With pyridine; trichlorophosphate In benzene for 10h; Reflux; Inert atmosphere; Stage #2: With water In acetone for 0.25h; Inert atmosphere; Reflux;	Synthesis of bis(2,4-dichloro-6-methylphenyl)phosphoric acid, (2,4-Cl2-6-MeC6H3O)2PO2H Phosphoryl chloride (3.7 ml, 6.13 g, 40 mmol) and then pyridine (7.1 ml, 6.96 g, 88 mmol) were added to a stirred solution of 2,4-dichloro-6-methylphenol (14.87 g, 84 mmol) in benzene (30 ml). The reaction mixture was refluxed for 10 h. Upon addition of water (15 ml), the reaction mixture was stirred for 15 min. The organic layer was separated from the aqueous phase. The solvent was removed on a rotary evaporator. The resulting white residue was hydrolyzed by adding acetone (50 ml) and water (5 ml), followed by refluxing for 15 min. After cooling to the room temperature, the formed precipitate was filtered off; washed with water (2 × 30 ml), acetone (1 × 10 ml), and hexane (2 × 30 ml); and dried under vacuum to constant mass (10.56 g). The organic layer of the remaining filtrate was separated from the aqueous phase, the solvent was evaporated. The obtained white precipitate was also filtered off; washed with water (2 × 30 ml), acetone (1 × 10 ml), dichloromethane (1 × 20 ml), and hexane (2 × 30 ml); and dried under vacuum to constant mass (5.06 g). The combined yield of white product was 15.62 g (37.55 mmol, 94%).

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1570-65-6 ]

Quality Control of [ 1570-65-6 ]

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[ 1570-65-6 ] Synthesis Path-Upstream 1~20

[ 1570-65-6 ] Synthesis Path-Downstream 1~69

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Aryls

Chlorides

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[ 1570-65-6 ]