[ CAS No. 60290-21-3 ] {[proInfo.proName]}

Name: 60290-21-3|4-Chloro-1H-pyrrolo[3,2-c]pyridine|95%
Brand: Ambeed
SKU: A278896
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Quality Control of [ 60290-21-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 60290-21-3 ]

Product Details of [ 60290-21-3 ]

CAS No. :	60290-21-3	MDL No. :	MFCD07781160
Formula :	C₇H₅ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	152.58	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 60290-21-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.1
TPSA :	28.68 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) :	-5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	1.94
Log Po/w (WLOGP) :	2.22
Log Po/w (MLOGP) :	1.18
Log Po/w (SILICOS-IT) :	2.71
Consensus Log Po/w :	1.89

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.67
Solubility :	0.323 mg/ml ; 0.00212 mol/l
Class :	Soluble
Log S (Ali) :	-2.17
Solubility :	1.04 mg/ml ; 0.00681 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.51
Solubility :	0.0472 mg/ml ; 0.000309 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 60290-21-3 ]

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

Application In Synthesis of [ 60290-21-3 ]

* 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 [ 60290-21-3 ]
Downstream synthetic route of [ 60290-21-3 ]

[ 60290-21-3 ] Synthesis Path-Upstream 1~6

1
[ 494767-29-2 ]
[ 60290-21-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With manganese(IV) oxide In tetrahydrofuranHeating / reflux	Intermediate 13-Bromo-4-chloro-lH-pyrrolo[3_No.2-c]pyridine; [00124] To a solution of the amine (2.18 g, 14.2 mmol) in THF (60 mL) was added Mnψ2 (7 g, 80.5 mmol) and the mixture was heated to reflux. After 5 h, a further portion of MnO₂ (3 g, 34.5 mmol) was added and stirring continued overnight. The reaction was filtered through Celite and concentrated to give a white solid (1.95 g, 91percent) .[00125] The indole (1.48 g, 9.72 mmol) was dissolved in CH2C12 (50 mL) and cooled to 0 ^aC under nitrogen. N- Bromosuccinimide (1.82 g, 10.2 mmol) was added and after 30 min the ice-bath was removed and stirring continued for a further 30 min. The desired bromide (1.53 g, 68percent) was filtered off and dried on high vacuum. MS (ES+) m/e = 231. IH NMR (DMSO) 7.48 (IH, d) , 7.80 (IH, s), 8.00 (lH, d) .

Reference： [1] Patent: WO2007/95223, 2007, A2, . Location in patent: Page/Page column 41

2
[ 54415-77-9 ]
[ 60290-21-3 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 2, p. 359 - 367
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3199 - 3203

3
[ 271-34-1 ]
[ 60290-21-3 ]

Reference： [1] Patent: WO2017/23987, 2017, A1,
[2] Patent: WO2017/24003, 2017, A1,
[3] Patent: WO2017/24010, 2017, A1,
[4] Patent: WO2017/23984, 2017, A1,

4
[ 109113-39-5 ]
[ 60290-21-3 ]

Reference： [1] Patent: WO2017/23987, 2017, A1,
[2] Patent: WO2017/24003, 2017, A1,
[3] Patent: WO2017/24010, 2017, A1,
[4] Patent: WO2017/23984, 2017, A1,

5
[ 26956-47-8 ]
[ 60290-21-3 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 2, p. 359 - 367

6
[ 557-21-1 ]
[ 60290-21-3 ]
[ 1040682-68-5 ]

Yield	Reaction Conditions	Operation in experiment
32%	With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; zinc In 1-methyl-pyrrolidin-2-one at 120℃; for 18 h; Inert atmosphere	step 1 : A mixture of 4-chloro-lH-pyrrolo[3,2-c]pyridine (500 mg, 3.28 mmol), zinc cyanide (422 mg, 3.61mmol), Pd₂(dba)₃ (600 mg, 0.656 mmol), dppf (729 mg, 1.312 mmol), and Zn powder (21 mg, 0.328 mmol) in NMP (30 mL) under nitrogen was stirred at 120 °C for 18 h. The reaction mixture was cooled, poured into water (150 mL), extracted with DCM (3 x 50 mL), dried (MgSO i), filtered and concentrated under reduced pressure. The crude residue was purified by S1O₂ chromatography eluting with petroleum ethenEtOAc (1 :1) as eluting solvents to afford 1H-pyrrolo[3,2-c]pyridine-4-carbonitrile as a white solid (150 mg, 32 percent). MS (ESI) m/z: 144.3 [M+l] ⁺.
11%	With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; zinc In 1-methyl-pyrrolidin-2-one at 120℃; for 18 h; Inert atmosphere	A mixture of 4-chloro-lH-pyrrolo[3,2-c]pyridine (0.5 g, 3.28 mmol, 1.0 eq), Zn(CN)2 (422 mg, 3.61 mmol, 1.1 eq) , Pd2(dba)3 (600.0 mg, 0.656 mmol, 0.2 eq), dppf (729.0 mg, 1.312 mmol, 0.4 eq), Zn (21.0 mg, 0.328 mmol, 0.1 eq) in MP (30.0 mL) was stirred at 120 °C for 18 h under Ar. After the reaction was complete, the mixture was extracted with EA. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (EA/PE = 1/1, v/v) to provide lH-pyrrolo[3,2-c] pyridine-4-carbonitrile (68.0 mg, 11percent).

Reference： [1] Patent: WO2013/92940, 2013, A1, . Location in patent: Page/Page column 38; 39
[2] Patent: WO2018/11628, 2018, A1, . Location in patent: Paragraph 00682

[ 60290-21-3 ] Synthesis Path-Downstream 1~88

1
[ 54415-77-9 ]
[ 60290-21-3 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In acetonitrile; at 110℃; for 0.0833333h;Microwave irradiation;	General procedure: A solution of 6,7-dimethoxyisoquinolin-1(2H)-one(200 mg, 0.97 mmol), phosphoryl trichloride (0.268 mL, 2.92 mmol) inacetonitrile (5 mL) was stirred at 110 C for 5 minutes under microwaveirradiation. The reaction was quenched with a saturated aqueous sodium bicarbonatesolution and stirred at ambient temperature for 1 h. It was filtered throughcelite and washed with ethyl acetate. The filtrate was concentrated to dryness.The crude material was purified by flash chromatography, eluting with heptanesand ethyl acetate (1:0 to 0:1) to give the desired product as a gum (99 mg,45.4 %).

Reference： [1]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 359 - 367
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3199 - 3203

2
[ 60290-21-3 ]
[ 271-34-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 359 - 367

3
[ 26956-47-8 ]
[ 60290-21-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 359 - 367

4
[ 60290-21-3 ]
1-(benzenesulfonyl)-4-chloro-1H-pyrrolo[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; tetra(n-butyl)ammonium hydrogen sulfate; benzenesulfonyl chloride; In dichloromethane;	A. 1-Benzenesulfonyl-<strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong> Benzenesulfonyl chloride (3 mL, 23.5 mmol) is added dropwise to a solution of tetrabutylammonium hydrogen sulfate (0.53 g, 1.56 mmol), sodium hydroxide (1.56 g, 38.9 mmol) and <strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong> (2.38 g, 15.6 mmol) (prepared according to Rasmussen, M. J. Het. Chem, 1992, 29, 359) in CH2Cl2. The mixture is stirred at room temperature for 4 hours the diluted with CH2Cl2 and washed with saturated NH4Cl solution and brine. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluding with 1% MeOH/CH2Cl2 to 2% MeOH/CH2Cl2 to afford the title product (3.21 g, 11 mmol) as a white solid. 1H NMR (CDCl3, 300 MHz) delta8.25 (d, 1H), 7.92(m, 1H), 7.90 (d, 1H), 7.83 (dd, 1H), 7.60-7.66 (m, 2H), 7.51 (m, 2H), 6.80 (dd, 1H). EI MS, [M]+=292, 294, Cl pattern.

Reference： [1]Patent: US6281227,2001,B1

5
[ 60290-21-3 ]
[ 947238-42-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	With N-Bromosuccinimide; In dichloromethane; at 0℃; for 1h;	Intermediate 13-Bromo-4-chloro-lH-pyrrolo[3No.2-c]pyridine; [00124] To a solution of the amine (2.18 g, 14.2 mmol) in THF (60 mL) was added Mntheta2 (7 g, 80.5 mmol) and the mixture was heated to reflux. After 5 h, a further portion of MnO2 (3 g, 34.5 mmol) was added and stirring continued overnight. The reaction was filtered through Celite and concentrated to give a white solid (1.95 g, 91%) .[00125] The indole (1.48 g, 9.72 mmol) was dissolved in CH2C12 (50 mL) and cooled to 0 aC under nitrogen. N- Bromosuccinimide (1.82 g, 10.2 mmol) was added and after 30 min the ice-bath was removed and stirring continued for a further 30 min. The desired bromide (1.53 g, 68%) was filtered off and dried on high vacuum. MS (ES+) m/e = 231. IH NMR (DMSO) 7.48 (IH, d) , 7.80 (IH, s), 8.00 (lH, d) .
68%	With N-Bromosuccinimide; In dichloromethane; at 0℃; for 1.5h;	The starting material 1 (1.48 g, 9.72 mmol) was dissolved in 50 mL of dichloromethane, and it was cooled to 0 C with an ice water bath, and then N-bromosuccinimide (1.82 g, 10.2 mmol) was added in portions. After an hour, the ice bath was removed and stirring was continued for another half an hour. The desired bromide was filtered off and dried under vacuum to obtain 1.53 g of the target compound. Yield: 68%.

Reference： [1]Patent: WO2007/95223,2007,A2 .Location in patent: Page/Page column 41
[2]Patent: CN110606848,2019,A .Location in patent: Paragraph 0033-0037

6
[ 494767-29-2 ]
[ 60290-21-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With manganese(IV) oxide; In tetrahydrofuran;Heating / reflux;	Intermediate 13-Bromo-4-chloro-lH-pyrrolo[3No.2-c]pyridine; [00124] To a solution of the amine (2.18 g, 14.2 mmol) in THF (60 mL) was added Mntheta2 (7 g, 80.5 mmol) and the mixture was heated to reflux. After 5 h, a further portion of MnO2 (3 g, 34.5 mmol) was added and stirring continued overnight. The reaction was filtered through Celite and concentrated to give a white solid (1.95 g, 91%) .[00125] The indole (1.48 g, 9.72 mmol) was dissolved in CH2C12 (50 mL) and cooled to 0 aC under nitrogen. N- Bromosuccinimide (1.82 g, 10.2 mmol) was added and after 30 min the ice-bath was removed and stirring continued for a further 30 min. The desired bromide (1.53 g, 68%) was filtered off and dried on high vacuum. MS (ES+) m/e = 231. IH NMR (DMSO) 7.48 (IH, d) , 7.80 (IH, s), 8.00 (lH, d) .

Reference： [1]Patent: WO2007/95223,2007,A2 .Location in patent: Page/Page column 41

7
[ 459-46-1 ]
[ 60290-21-3 ]
[ 1160359-96-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium hydride; In N,N-dimethyl-formamide; at 20℃;	To 4-Chloro-5-azaindote (120 mg, 0.79 mmol) in 5 ml DMF was added 4- Fluorobenzylbromide (0.120 ml, 0.95 mmol) then add NaH (32 mg, 0.79 mmol) and <n="193"/>stir at room temperature overnight. Work up reaction by adding water and EtOAc then extract three times with EtOAc. Pool all organics and wash one time with brine then dry over sodium sulfate, filter and concentrate to dryness. The residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50) to provide 100 mg (50%) of product

Reference： [1]Patent: WO2009/73777,2009,A1 .Location in patent: Page/Page column 190-191

8
[ 1190841-67-8 ]
[ 60290-21-3 ]
4-methoxy-N-methyl-5-{(1S)-1-methyl-2-[(2R)-2-methyl-4-(1H-pyrrolo[3,2-c]pyridin-4-yl)piperazin-1-yl]-2-oxoethoxy}pyridine-2-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5250 - 5255

9
[ 824-94-2 ]
[ 60290-21-3 ]
[ 1313714-53-2 ]

Yield	Reaction Conditions	Operation in experiment
82%		Compound 14a (125 mg, 0.82 mmol) was dissolved in DMF (3.0 mL) and cooled to 0 C. NaH (ca. 60%, 43 mg, ca. 1.07 mmol) was added and reaction mixture was stirred under N2 for 1 h before 4-methoxybenzyl chloride (0.13 mL, 0.98 mmol) was added. The reaction mixture was stirred for 1.5 h while reaching ambient temperature and quenched by adding few drops of water. The mixture was poured into water (25 mL) and extracted with EtOAc (2 × 30 mL). The combined organic layers were dried (MgSO4) and evaporated in vacuo. The product was purified by flash chromatography on silica gel eluting with hexane followed by CH2Cl2-hexane (1:1); and finally CH2Cl2; yield 165 mg (82%), colorless wax. 1H NMR (CDCl3, 300 MHz) delta 3.76 (s, 3H, OCH3), 5.22 (s, 2H, CH2), 6.65 (d, J = 3.2 Hz, 1H, H-3), 6.83 (d, J = 8.6 Hz, 2H, Ar), 7.03 (d, J = 8.5 Hz, 2H, Ar), 7.12-7.24 (m, 2H, H-2 and H-7), 8.02 (d, J = 5.8 Hz, 1H, H-6); 13C NMR (CDCl3, 75 MHz) delta 50.2 (CH2), 55.3 (OCH3), 101.6 (C-3), 104.9 (C-7), 114.4 (CH in Ar), 123.8 (C-3a), 127.8 (C-1 in Ar), 128.3 (CH in Ar), 129.5 (C-2), 139.7 (C-6), 141.0 (C-4), 144.0 (C-7a), 159.5 (C-4 in Ar); MS EI m/z (rel %) 274/272 (7/22 M+), 122 (10), 121 (100), 78 (6); HRMS Found 272.0716, calcd for C15H13ClN2O 272.0716.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3483 - 3491

10
[ 824-94-2 ]
[ 60290-21-3 ]
[ 1313714-40-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3483 - 3491

11
[ 557-21-1 ]
[ 60290-21-3 ]
[ 1040682-68-5 ]

Yield	Reaction Conditions	Operation in experiment
32%	With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); zinc; In 1-methyl-pyrrolidin-2-one; at 120℃; for 18h;Inert atmosphere;	step 1 : A mixture of 4-chloro-lH-pyrrolo[3,2-c]pyridine (500 mg, 3.28 mmol), zinc cyanide (422 mg, 3.61mmol), Pd2(dba)3 (600 mg, 0.656 mmol), dppf (729 mg, 1.312 mmol), and Zn powder (21 mg, 0.328 mmol) in NMP (30 mL) under nitrogen was stirred at 120 C for 18 h. The reaction mixture was cooled, poured into water (150 mL), extracted with DCM (3 x 50 mL), dried (MgSO i), filtered and concentrated under reduced pressure. The crude residue was purified by S1O2 chromatography eluting with petroleum ethenEtOAc (1 :1) as eluting solvents to afford 1H-pyrrolo[3,2-c]pyridine-4-carbonitrile as a white solid (150 mg, 32 %). MS (ESI) m/z: 144.3 [M+l] +.
11%	With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); zinc; In 1-methyl-pyrrolidin-2-one; at 120℃; for 18h;Inert atmosphere;	A mixture of 4-chloro-lH-pyrrolo[3,2-c]pyridine (0.5 g, 3.28 mmol, 1.0 eq), Zn(CN)2 (422 mg, 3.61 mmol, 1.1 eq) , Pd2(dba)3 (600.0 mg, 0.656 mmol, 0.2 eq), dppf (729.0 mg, 1.312 mmol, 0.4 eq), Zn (21.0 mg, 0.328 mmol, 0.1 eq) in MP (30.0 mL) was stirred at 120 C for 18 h under Ar. After the reaction was complete, the mixture was extracted with EA. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (EA/PE = 1/1, v/v) to provide lH-pyrrolo[3,2-c] pyridine-4-carbonitrile (68.0 mg, 11%).

Reference： [1]Patent: WO2013/92940,2013,A1 .Location in patent: Page/Page column 38; 39
[2]Patent: WO2018/11628,2018,A1 .Location in patent: Paragraph 00682

12
[ 97674-02-7 ]
[ 60290-21-3 ]
C₁₁H₁₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); In 1-methyl-pyrrolidin-2-one; at 140℃; for 18h;Inert atmosphere;	step 1 : A mixture of <strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong> (1.0 g, 6.58 mmol), Pd(PPh3)4 (763 mg, 0.66 mmol), and tributyl(l-ethoxyvinyl)stannane (2.61 g, 7.23 mmol) in NMP (20 mL) was stirred under N2 at 140 C for 18 h. The reaction mixture was poured into aqueous HCl solution (2 N, 150 mL), stirred at RT for 2 h, and washed with DCM (50 mL x 3). The aqueous layer was adjusted to pH 8 with NaHC03 (solid), extracted with EtOAc (50 mL x 3), and concentrated under reduced pressure to afford 680 mg (64.6%) of 1-(1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone as yellow solid: MS (ESI) m/z: 161.1 [M+l]+.

Reference： [1]Patent: WO2013/92940,2013,A1 .Location in patent: Page/Page column 39

13
[ 60290-21-3 ]
4-chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 18h;	NIS (767.0 mg, 3.441 mmol, 1.5 eq) was added to a solution of 4-chloro-lH- pyrrolo[3,2-c]pyridine (350.0 mg, 2.294 mmol, 1.0 eq) in DMF (15.0 mL) at 0 C. The reaction mixture was stirred at rt for 18 h, then concentrated in vacuo and purified via column chromatography (0 ~ 50% ethyl acetate in petroleum ether) to provide 4-chloro-3- iodo-lH-pyrrolo[3,2-c]pyridine (618.0 mg, 97%).
81%	With N-chloro-succinimide; In N,N-dimethyl-formamide; at 23℃; for 2.5h;Cooling with ice;	To a pale grey solution of commercially available 4-Choro-5- azaindole (3.34 g, 21.89 mmol) in DMF (Volume: 20 ml), was added N- iodosuccinimide (5.17 g, 22.98 mmol) in one portion at 20-23C. The solution was agitated at 23C for 2h. The addition is slightly exothermic (+5C) and the mixture went from a white suspension to pale brown solution in 5 min. The mixture was poured onto ice cold water (2 x 250 mL) with agitation. After 30 min, the reaction was filtered and washed with water (2 x 1 L). The wet cake was diluted with acetonitrile (50 ml_), agitated for 10 min in an ice bath, filtered and rinsed with 200 ml_ hexanes. The wet cake was dried under vacuum at 50 C for 1 h followed by vacuum drying to give the desired product, 4-chloro-3- iodo-1 H-pyrrolo[3,2-c]pyridine (A-6) (5.2 g, 17.74 mmol, 81 % yield) - pale brown solid. 1 H NMR (500MHz, DMSO-d6) d = 12.34 (br. s., 1 H), 8.04 (d, J=5.6 Hz, 1 H), 7.83 (d, J=2.3 Hz, 1 H), 7.56 (d, J=5.6 Hz, 1 H) LC-MS: m/z 393 (M + H).
455 mg	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 1h;	4-Chloro-1H-pyrrolo[3,2-c]pyridine (247 mg) synthesized by the method disclosed in was dissolved in DMF (7.0 ml). After cooling to 0C, N-iodosuccinimide (382 mg) was added thereto. The resulting mixture was stirred at room temperature for 1 hour, and then chloroform and water were added thereto to separate the organic layer. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a darkbrown solid (455 mg). Physical properties: m/z[M+H]+ 279.1

455 mg	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 1h;	4-Chloro-1H-pyrrolo[3,2-c]pyridine (247 mg) synthesized by the method disclosed in WO2007/095223 was dissolved in DMF (7.0 ml). After cooling to 0 C., N-iodosuccinimide (382 mg) was added thereto. The resulting mixture was stirred at room temperature for 1 hour, and then chloroform and water were added thereto to separate the organic layer. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a dark-brown solid (455 mg). Physical properties: m/z[M+H]+ 279.1
455 mg	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 1h;	4-Chloro-1H-pyrrolo[3,2-c]pyridine (247 mg) synthesized by the method disclosed in WO2007/095223 was dissolved in DMF (7.0 ml). After cooling to 0 C., N-iodosuccinimide (382 mg) was added thereto. The resulting mixture was stirred at room temperature for 1 hour, and then chloroform and water were added thereto to separate the organic layer. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a dark-brown solid (455 mg). Physical properties: m/z [M+H]+ 279.1

Reference： [1]Patent: WO2018/11628,2018,A1 .Location in patent: Paragraph 00614
[2]Patent: WO2019/153080,2019,A1 .Location in patent: Paragraph 00218
[3]Patent: EP2657233,2013,A1 .Location in patent: Paragraph 0320
[4]Patent: US2016/136168,2016,A1 .Location in patent: Paragraph 0409
[5]Patent: US2016/193210,2016,A1 .Location in patent: Paragraph 0412

14
[ 60290-21-3 ]
tert-butyl (S)-3-(4-chloro-3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: EP2657233,2013,A1
[2]Patent: US2016/136168,2016,A1

15
[ 60290-21-3 ]
tert-butyl (S)-3-(4-chloro-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrrolo[3,2-c]pyridin-1-yl)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: EP2657233,2013,A1
[2]Patent: US2016/136168,2016,A1
[3]Patent: US2016/193210,2016,A1

16
[ 60290-21-3 ]
tert-butyl (S)-3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrrolo[3,2-c]pyridin-1-yl)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: EP2657233,2013,A1
[2]Patent: US2016/136168,2016,A1
[3]Patent: US2016/193210,2016,A1

17
[ 24424-99-5 ]
[ 60290-21-3 ]
[ 1609259-26-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dmap; In acetonitrile; at 20℃; for 18h;	Preparation P2 tert-Butyl <strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong>-1-carboxylate (P2) Di-tert-butyl dicarbonate (99%, 650 mg, 2.95 mmol) was added to a solution of <strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong> (300 mg, 1.97 mmol) and 4-(dimethylamino)pyridine (97%, 124 mg, 0.984 mmol) in acetonitrile (3 mL), and the reaction mixture was stirred at room temperature for 18 hours. Volatiles were removed in vacuo, and the residue was purified via chromatography on silica gel (Gradient: 0% to 50% ethyl acetate in heptane) to afford the product as a white solid. Yield: 410 mg, 1.62 mmol, 82%. LCMS m/z 253.0 [M+H+]. 1H NMR (400 MHz, CDCl3) delta 8.24 (d, J=5.7 Hz, 1H), 7.95 (br d, J=5.7 Hz, 1H), 7.65 (d, J=3.7 Hz, 1H), 6.72 (dd, J=3.7, 0.8 Hz, 1H), 1.70 (s, 9H).

Reference： [1]Patent: US2014/128374,2014,A1 .Location in patent: Paragraph 0315; 0316

18
[ 60290-21-3 ]
[ 1609259-40-6 ]

Reference： [1]Patent: US2014/128374,2014,A1

19
[ 60290-21-3 ]
[ 1609259-41-7 ]

Reference： [1]Patent: US2014/128374,2014,A1

20
[ 60290-21-3 ]
[ 1609259-42-8 ]

Reference： [1]Patent: US2014/128374,2014,A1

21
[ 60290-21-3 ]
[ 1609258-88-9 ]

Reference： [1]Patent: US2014/128374,2014,A1

22
[ 60290-21-3 ]
[ 1609259-43-9 ]

Reference： [1]Patent: US2014/128374,2014,A1

23
[ 60290-21-3 ]
[ 1609259-44-0 ]

Reference： [1]Patent: US2014/128374,2014,A1

24
[ 60290-21-3 ]
[ 1609259-56-4 ]

Reference： [1]Patent: US2014/128374,2014,A1

25
[ 60290-21-3 ]
[ 1609259-57-5 ]

Reference： [1]Patent: US2014/128374,2014,A1

26
[ 60290-21-3 ]
[ 1609258-90-3 ]

Reference： [1]Patent: US2014/128374,2014,A1

27
[ 60290-21-3 ]
[ 1609259-59-7 ]

Reference： [1]Patent: US2014/128374,2014,A1

28
[ 60290-21-3 ]
[ 1609258-92-5 ]

Reference： [1]Patent: US2014/128374,2014,A1

29
[ 60290-21-3 ]
[ 1609259-34-8 ]

Reference： [1]Patent: US2014/128374,2014,A1

30
[ 60290-21-3 ]
[ 1609259-35-9 ]

Reference： [1]Patent: US2014/128374,2014,A1

31
[ 516-12-1 ]
[ 60290-21-3 ]
4-chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In N,N-dimethyl-formamide; at 0 - 20℃; for 18h;	Step 1. Synthesis of 4-chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine (C6) N-Iodosuccinimide (1.3 g, 5.8 mmol) was added to a 0 C. solution of <strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong> (0.60 g, 3.9 mmol) in N,N-dimethylformamide (10 mL). The reaction mixture was stirred at room temperature for 18 hours, whereupon it was concentrated in vacuo. Purification via silica gel chromatography (0% to 50% ethyl acetate in petroleum ether) afforded the product as a yellow solid. Yield: 900 mg, 3.2 mmol, 82%. 1H NMR (400 MHz, CDCl3) delta 8.10 (d, J=5.5 Hz, 1H), 7.42 (d, J=2.5 Hz, 1H), 7.34 (d, J=5.8 Hz, 1H).

Reference： [1]Patent: US2014/128374,2014,A1 .Location in patent: Paragraph 0330; 0331

32
[ 76513-69-4 ]
[ 60290-21-3 ]
[ 1609259-25-7 ]

Yield	Reaction Conditions	Operation in experiment
72%		Preparation P1 4-Chloro-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[3,2-c]pyridine (P1) A mixture of <strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong> (98%, 2.0 g, 13 mmol) and tetrahydrofuran (20 mL) was cooled to 0 C. Sodium hydride (60% in oil, 1.03 g, 25.8 mmol) was added portion-wise over 5 minutes, and the reaction mixture was allowed to stir at 0 C. for 10 minutes. 2-(Trimethylsilyl)ethoxymethyl chloride (3.40 mL, 19.3 mmol) was then added drop-wise over 5 minutes, and stirring was continued at 0 C. for 15 minutes. The reaction mixture was quenched with saturated aqueous ammonium chloride solution; the aqueous layer was extracted twice with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 10% to 20% ethyl acetate in heptane) afforded the product as a colorless oil. Yield: 2.64 g, 9.33 mmol, 72%. LCMS m/z 283.0 [M+H+]. 1H NMR (400 MHz, CDCl3) delta 8.13 (d, J=5.8 Hz, 1H), 7.34 (dd, J=5.8, 0.7 Hz, 1H), 7.25 (d, J=3.3 Hz, 1H), 6.69 (dd, J=3.3, 0.7 Hz, 1H), 5.48 (s, 2H), 3.46 (dd, J=8.2, 8.1 Hz, 2H), 0.89 (dd, J=8.2, 8.1 Hz, 2H), -0.05 (s, 9H).

Reference： [1]Patent: US2014/128374,2014,A1 .Location in patent: Paragraph 0313; 0314

33
[ 60290-21-3 ]
[ 1609259-45-1 ]

Reference： [1]Patent: US2014/128374,2014,A1

34
[ 60290-21-3 ]
[ 1609258-89-0 ]

Reference： [1]Patent: US2014/128374,2014,A1

35
[ 60290-21-3 ]
[ 1609259-04-2 ]

Reference： [1]Patent: US2014/128374,2014,A1

36
[ 367-27-1 ]
[ 60290-21-3 ]
[ 1613479-43-8 ]

Yield	Reaction Conditions	Operation in experiment
60.7%	With sodium hydride; In N,N-dimethyl acetamide; mineral oil; at 250℃; for 0.05h;Inert atmosphere; Microwave irradiation;	A solution of <strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong>(100 mg, 0.66 mmol) and 2,4-difluorophenol (213 mg, 1.64mmol) in DMA (2 mL) was stirred for 5 minutes under nitrogen. Sodium hydride (26.2 mg, 0.66 mmol; 60% inmineral oil) was heated with stirring at 250C for 3 minutesunder microwave irradiation. The mixture was diluted with THF (10 mL) and quenched with water and ice (2 mL). The solution was filtered through a VarianChemElute cartridge and concentrated to dryness. The material was partially purified by flash chromatography with gradient elution of heptane and ethyl acetate (1:0 to 0:1) to give a gum. The material was further purified by reverse phase preparative HPLC to provide the desired product (49.0 mg, 60.7 %) as asolid. HPLC purity: >99% (215 nM),>99% (254 nM), >99% (280 nM). 1H NMR (400 MHz, DMSO-d6) d ppm 6.63 (dd, J=3.3, 1.0 Hz, 1 H) 7.08 - 7.19 (m, 2 H) 7.35 - 7.46(m, 3 H) 7.58 (d, J=5.9 Hz, 1 H). HRMS m/z calcd for C13H8F2N2O[M+H]+ 247.0677, found 247.0678.
60.7%		A solution of <strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong>(100 mg, 0.66 mmol) and 2,4-difluorophenol (213 mg, 1.64 mmol) in DMA (2 mL)was stirred for 5 minutes under nitrogen.Sodium hydride (26.2 mg, 0.66 mmol; 60% in mineral oil) was heated withstirring at 250 C for 3 minutes under microwave irradiation. The mixture was dilutedwith THF (10 mL) and quenched with water and ice (2 mL). The solution wasfiltered through a Varian ChemElute cartridge and concentrated to dryness. The materialwas partially purified by flash chromatography with gradient elution of heptaneand ethyl acetate (1:0 to 0:1) to give a gum. The material was further purifiedby reverse phase preparative HPLC to provide the desired product (49.0 mg, 60.7%) as a solid. HPLC purity: >99% (215nM), >99% (254 nM), >99% (280 nM). 1H NMR (400 MHz, DMSO-d6) d ppm 6.63 (dd, J=3.3, 1.0 Hz, 1 H) 7.08 - 7.19 (m, 2 H) 7.35 - 7.46(m, 3 H) 7.58 (d, J=5.9 Hz, 1 H). HRMS m/z calcd for C13H8F2N2O[M+H]+ 247.0677, found 247.0678.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3199 - 3203
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3199 - 3203

37
[ 371-41-5 ]
[ 60290-21-3 ]
[ 1613479-49-4 ]

Yield	Reaction Conditions	Operation in experiment
27.4%	With sodium hydride; In N,N-dimethyl acetamide; mineral oil; at 250℃; for 0.25h;Inert atmosphere; Microwave irradiation;	A solution of <strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong>(100 mg, 0.66 mmol) and 4-fluorophenol (367 mg, 3.28 mmol) in DMA(2.0 mL) was stirred under nitrogen. Sodium hydride (52.4 mg, 1.31 mmol; 60% in mineral oil) was added to the solution and then stirred for 5 minutes before heating under microwave irradiation at 250C for 10 minutes. The mixture was diluted withTHF (10 mL) and quenched with water and ice (2 mL). The solution was filtered through a Varian ChemElute cartridge and concentrated. The material was partially purified by flash chromatography with a gradient elution of heptane,ethyl acetate and methanol (1:1:0 to 1:1:1) to give a gum. The material was further purified by reverse phase preparative HPLC to provide the desired material (41.0mg, 27.4 %) as a solid. HPLC Purity: >99%(215 nM), >98% (254 nM), >99% (280 nM). 1H NMR (400 MHz, DMSO-d6) d ppm 6.55 (dd, J=3.1,0.8 Hz, 1 H), 7.10 - 7.28 (m, 5 H), 7.41 (d, J=3.1 Hz, 1 H), 7.59 - 7.69 (m, 1H), 11.65 (br. s., 1 H). HRMS m/z calcd for C13H9FN2O[M+H]+ 229.0775, found 229.0772.
27.4%	With sodium hydride; In N,N-dimethyl acetamide; mineral oil; at 250℃; for 0.166667h;Inert atmosphere; Microwave irradiation;	A solution of <strong>[60290-21-3]4-chloro-1H-pyrrolo[3,2-c]pyridine</strong>(100 mg, 0.66 mmol) and 4-fluorophenol (367 mg, 3.28 mmol) in DMA (2.0 mL) wasstirred under nitrogen. Sodium hydride (52.4 mg, 1.31 mmol; 60% in mineral oil)was added to the solution and then stirred for 5 minutes before heating under microwaveirradiation at 250 Cfor 10 minutes. The mixture was diluted with THF (10 mL) and quenched withwater and ice (2 mL). The solution was filtered through a Varian ChemElutecartridge and concentrated. The material was partially purified by flashchromatography with a gradient elution of heptane, ethyl acetate and methanol(1:1:0 to 1:1:1) to give a gum. The material was further purified by reversephase preparative HPLC to provide the desired material (41.0 mg, 27.4 %) as asolid. HPLC Purity: >99% (215 nM), >98% (254 nM), >99% (280 nM). 1HNMR (400 MHz, DMSO-d6) d ppm 6.55 (dd, J=3.1, 0.8 Hz, 1 H), 7.10 - 7.28 (m, 5 H), 7.41 (d,J=3.1 Hz, 1 H), 7.59 - 7.69 (m, 1 H), 11.65 (br. s., 1 H). HRMSm/z calcd for C13H9FN2O [M+H]+ 229.0775,found 229.0772.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3199 - 3203
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3199 - 3203

38
[ 10406-25-4 ]
[ 60290-21-3 ]
4-[(1H-pyrrolo[3,2-c]pyridin-4-ylamino)methyl]benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
300 mg	In ethanol; at 130℃; for 35h;Inert atmosphere;	Example 7C. 4-[(lH-Pyrrolo[3,2-c]pyridin-4-ylamino)-methyl]-benzonitrile4-(Aminomethyl)benzonitrile.HCI was partitioned between chloroform (50 mL) and saturated NaHC03 (10 mL), dried over Na2S04, filtered and evaporated to afford 4-(aminomethyl)benzonitrile free base as a yellow oil. To 4-(aminomethyl)benzonitrile (250mg, 1.89mmol) was added <strong>[60290-21-3]4-chloro-5-azaindole</strong> (289mg, 1.89mmol) in ethanol (1 mL) and the mixture was heated at 130 C for 35 hours, adding minimum ethanol when evaporated. The crude residue was purified by flash chromatography eluting with 4% to 12% MeOH-DCM to give a pale yellow gum identified as the title compound (300mg, 1.21mmol, 64% yield). [M+H]+ = 248.7

Reference： [1]Patent: WO2015/22547,2015,A1 .Location in patent: Page/Page column 23

39
(5-(pyrrolidine-1-carbonyl)pyridin-3-yl)boronic acid [ No CAS ]
[ 60290-21-3 ]
4-(5-((pyrrolidin-1-yl)methanonyl)pyridin-3-yl)-1H-pyrrolo[3,2-c]pyridine [ No CAS ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 266 - 275

40
[ 60290-21-3 ]
tert-butyl 4-(1-(4-(methoxycarbonyl)benzyl)-1H-pyrrolo[3.2-c]pyridin-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/87151,2015,A1

41
[ 60290-21-3 ]
tert-butyl 4-(1-(4-(hydroxycarbamoyl)benzyl)-1H-pyrrolo[3.2-c]pyridin-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/87151,2015,A1

42
[ 2417-72-3 ]
[ 60290-21-3 ]
methyl 4-((4-chloro-1H-pyrrolo[3,2-c]pyridin-1-yl)methyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.2%	With potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 12h;	The compound of formula 11-i (4-chioro- I H-pyrrolo[3,2-c]pyridine) (0.300 g, 1.966mmol), methyl 4-(bromoethyl)benzoate (0.495 g, 2.163 mmol) and potassium hydroxide (0.132 g, 2.359 mmol) were dissolved in N,N-dimethylformamide (10 mL) at room temperature, and the solution was stirred at the same temperature for 12 hours. Then, the reaction mixture was concentrated under reduced pressure to remove the solvent, and water (20 mL) was added to the concentrate, followed by stirring. Then, the precipitated solid was filtered, washed with water, and dried, thereby obtaining the desired compound of formula 11-2 (0.497 g, 84.2 %) as a white solid.

Reference： [1]Patent: WO2015/87151,2015,A1 .Location in patent: Paragraph 664; 665

43
1-(benzenesulfonyl)-4-chloro-1H-pyrrolo[3,2-c]pyridine [ No CAS ]
[ 60290-21-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide; In methanol; water; at 60℃; for 3h;	To a solution of 4-chloro-l-(phenylsulfonyl)-lH-pyrrolo[3,2-c]pyridine (LXXVIII) (0.62 g, 2.1 mmol) in MeOH (10 mL) was added 2N aqueous NaOH (2 mL) at room temperature. The solution was heated at 60C for 3 h. Water (15 mL) was added and extracted with DCM (x 2). Removal of DCM gave 4-chloro-lH-pyrrolo[3,2-c]pyridine (LXXIX) as a white solid (320 mg, 2.10 mmol, 99.0% yield). NMR (DMSO-< 400 MHz) delta ppm 6.59 (d, J=2.4Hz, IH), 7.48 (d, J=5.6Hz, IH), 7.60 (d, J=3.2Hz, IH), 8.00 (d, J=5.6Hz, IH); ESIMS found for C7H5CIN2 mlz 153.0 (M+H).
99%	With sodium hydroxide; In methanol; water; at 60℃; for 3h;	To a solution of 4-chloro-l-(phenylsulfonyl)-lH-pyrrolo[3,2-c]pyridine (LXXVIII) (0.62 g, 2.1 mmol) in Me OH (10 mL) was added 2N aqueous NaOH (2 mL) at room temperature. The solution was heated at 60C for 3 h. Water (15 mL) was added and extracted with DCM (x 2). Removal of DCM gave 4-chloro-lH-pyrrolo[3,2-c]pyridine (LXXIX) as a white solid (320 mg, 2.10 mmol, 99.0% yield). NMR DMSO-d6, 400 MHz) delta ppm 6.59 (d, J=2.4Hz, IH), 7.48 (d, J=5.6Hz, IH), 7.60 (d, J=3.2Hz, IH), 8.00 (d, J=5.6Hz, IH); ESIMS found for C7H5C1N2 mlz 153.0 (M+H).
99%	With water; sodium hydroxide; In methanol; at 60℃; for 3h;	To a solution of 4-chloro-l-(phenylsulfonyl)-lH-pyrrolo[3,2-c]pyridine (XCV) (0.62 g, 2.1 mmol) in MeOH (10 mL) was added 2N aqueous NaOH (2 mL) at room temperature. The solution was heated at 60C for 3 h. Water (15 mL) was added and extracted with DCM (x 2). Removal of DCM gave 4-chloro-lH-pyrrolo[3,2-c]pyridine (XCVI) as a white solid (320 mg, 2.10 mmol, 99.0% yield). NMR (DMSO-< 400 MHz) delta ppm 6.59 (d, J=2.4Hz, 1H), 7.48 (d, J=5.6Hz, 1H), 7.60 (d, J=3.2Hz, 1H), 8.00 (d, J=5.6Hz, 1H); ESIMS found for C7H5CIN2 mlz 153.0 (M+H).

99%

With water; sodium hydroxide; In methanol; at 60℃; for 3h;

Step 4 [0678] To a solution of 4-chloro-l-(phenylsulfonyl)-lH-pyrrolo[3,2-c]pyridine (LXXVIII) (0.62 g, 2.1 mmol) in MeOH (10 mL) was added 2N aqueous NaOH (2 mL) at room temperature. The solution was heated at 60C for 3 h. Water (15 mL) was added and extracted with DCM (x 2). Removal of DCM gave 4-chloro-lH-pyrrolo[3,2-c]pyridine (LXXIX) as a white solid (320 mg, 2.10 mmol, 99.0% yield). NMR DMSO-d6, 400 MHz) delta ppm 6.59 (d, J=2.4Hz, IH), 7.48 (d, J=5.6Hz, IH), 7.60 (d, J=3.2Hz, IH), 8.00 (d, J=5.6Hz, IH); ESIMS found for C7H5CIN2 mlz 153.0 (M+H).

Reference： [1]Patent: WO2017/23987,2017,A1 .Location in patent: Paragraph 0675; 0679
[2]Patent: WO2017/24003,2017,A1 .Location in patent: Paragraph 0675; 0679
[3]Patent: WO2017/24010,2017,A1 .Location in patent: Paragraph 0622; 0626
[4]Patent: WO2017/23984,2017,A1 .Location in patent: Paragraph 0678

44
[ 60290-21-3 ]
tert-butyl 4-(3-fluorophenyl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/23987,2017,A1
[2]Patent: WO2017/24003,2017,A1
[3]Patent: WO2017/24010,2017,A1
[4]Patent: WO2017/23984,2017,A1

45
[ 60290-21-3 ]
(1-(tert-butoxycarbonyl)-4-(3-fluorophenyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)boronic acid [ No CAS ]

Reference： [1]Patent: WO2017/23987,2017,A1
[2]Patent: WO2017/24003,2017,A1
[3]Patent: WO2017/24010,2017,A1
[4]Patent: WO2017/23984,2017,A1

46
[ 768-35-4 ]
[ 60290-21-3 ]
4-(3-fluorophenyl)-1H-pyrrolo[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.9%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 25 - 100℃; for 2h;Inert atmosphere;	To a solution of 4-chloro-lH-pyrrolo[3,2-c]pyridine (LXXIX) (13.3 g, 87.2 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (LXXX) (1.59 g, 113.3 mmol, 1.3 eq) in a solution of dioxane (80 mL) and water (27 mL) was added K3PO4 (46.3 g, 218 mmol, 2.5 eq) in one portion at 25C under N2. Then Pd(dppf)Cl2 (5.1 g, 6.97 mmol, 0.08 eq) was added under N2 atmosphere. The yellow solution was heated to 90-100C and stirred for 2 h. The reaction was added into water (500 mL), and the resultant solution was extracted with EtOAc (300 mL x 3). The organic layers were washed with brine (200 mL), dried over Na2S04 and concentrated to give a residue. The residue was purified by chromatography on silica gel to give 4-(3-fluorophenyl)-lH-pyrrolo[3,2- c]pyridine (LXXXI) as a red solid (10.9 g, 51.4 mmol, 58.9% yield). NMR (DMSO-£, 400 MHz) delta ppm 6.80 (s, IH), 7.24 - 7.33 (m, IH), 7.42 (d, J=6Hz, IH), 7.52 - 7.63 (m, 2H), 7.76 (d, J=8Hz, IH), 7.87 (d, J=7.6Hz, IH), 8.28 (d, J=5.6Hz, IH), 11.71 (brs, IH); ESIMS found for C13H9FN2 mlz 213.1 (M+H).
58.9%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 90 - 100℃; for 2h;Inert atmosphere;	To a solution of 4-chloro-lH-pyrrolo[3,2-c]pyridine (LXXIX) (13.3 g, 87.2 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (LXXX) (1.59 g, 113.3 mmol, 1.3 eq) in a solution of dioxane (80 mL) and water (27 mL) was added K3PO4 (46.3 g, 218 mmol, 2.5 eq) in one portion at 25C under N2. Then Pd(dppf)Cl2 (5.1 g, 6.97 mmol, 0.08 eq) was added under N2 atmosphere. The yellow solution was heated to 90-100C and stirred for 2 h. The reaction was added into water (500 mL), and the resultant solution was extracted with EtOAc (300 mL x 3). The organic layers were washed with brine (200 mL), dried over Na2SC>4 and concentrated to give a residue. The residue was purified by chromatography on silica gel to give 4-(3-fluorophenyl)- lH-pyrrolo[3,2-c]pyridine (LXXXI) as a red solid (10.9 g, 51.4 mmol, 58.9% yield). NMR (DMSO-£, 400 MHz) delta ppm 6.80 (s, 1H), 7.24 - 7.33 (m, 1H), 7.42 (d, J=6Hz, 1H), 7.52 - 7.63 (m, 2H), 7.76 (d, J=8Hz, 1H), 7.87 (d, J=7.6Hz, 1H), 8.28 (d, J=5.6Hz, 1H), 11.71 (brs, 1H); ESIMS found for Ci3H9FN2 mlz 213.1 (M+H).
58.9%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 25 - 100℃; for 2h;Inert atmosphere;	To a solution of 4-chloro-lH-pyrrolo[3,2-c]pyridine (XCVI) (13.3 g, 87.2 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (XCVII) (1.59 g, 113.3 mmol, 1.3 eq) in a solution of dioxane (80 mL) and water (27 mL) was added K3PO4 (46.3 g, 218 mmol, 2.5 eq) in one portion at 25C under N2. Then Pd(dppf)Cl2 (5.1 g, 6.97 mmol, 0.08 eq) was added under N2 atmosphere. The yellow solution was heated to 90-100C and stirred for 2 h. The reaction was added into water (500 mL), and the resultant solution was extracted with EtOAc (300 mL x 3). The organic layers were washed with brine (200 mL), dried over Na2S04 and concentrated to give a residue. The residue was purified by chromatography on silica gel to give 4-(3-fluorophenyl)-lH-pyrrolo[3,2- c]pyridine (XCVIII) as a red solid (10.9 g, 51.4 mmol, 58.9% yield). NMR (DMSO-£, 400 MHz) delta ppm 6.80 (s, IH), 7.24 - 7.33 (m, IH), 7.42 (d, J=6Hz, IH), 7.52 - 7.63 (m, 2H), 7.76 (d, J=8Hz, IH), 7.87 (d, J=7.6Hz, IH), 8.28 (d, J=5.6Hz, IH), 11.71 (brs, IH); ESIMS found for C13H9FN2 mlz 213.1 (M+H).

58.9%

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 25 - 100℃; for 2h;Inert atmosphere;

Step 1 [0680] To a solution of 4-chloro-lH-pyrrolo[3,2-c]pyridine (LXXIX) (13.3 g, 87.2 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (LXXX) (1.59 g, 113.3 mmol, 1.3 eq) in a solution of dioxane (80 mL) and water (27 mL) was added K3PO4 (46.3 g, 218 mmol, 2.5 eq) in one portion at 25C under N2. Then Pd(dppf)Cl2 (5.1 g, 6.97 mmol, 0.08 eq) was added under N2 atmosphere. The yellow solution was heated to 90-100C and stirred for 2 h. The reaction was added into water (500 mL), and the resultant solution was extracted with EtOAc (300 mL x 3). The organic layers were washed with brine (200 mL), dried over Na2SC>4 and concentrated to give a residue. The residue was purified by chromatography on silica gel to give 4-(3-fluorophenyl)- lH-pyrrolo[3,2-c]pyridine (LXXXI) as a red solid (10.9 g, 51.4 mmol, 58.9% yield). NMR (DMSO-£, 400 MHz) delta ppm 6.80 (s, 1H), 7.24 - 7.33 (m, 1H), 7.42 (d, J=6Hz, 1H), 7.52 - 7.63 (m, 2H), 7.76 (d, J=8Hz, 1H), 7.87 (d, J=7.6Hz, 1H), 8.28 (d, J=5.6Hz, 1H), 1 1.71 (brs, 1H); ESIMS found for C13H9FN2 mlz 213.1 (M+H).

Reference： [1]Patent: WO2017/23987,2017,A1 .Location in patent: Paragraph 0680; 0681
[2]Patent: WO2017/24003,2017,A1 .Location in patent: Paragraph 0680; 0681
[3]Patent: WO2017/24010,2017,A1 .Location in patent: Paragraph 0627; 0628
[4]Patent: WO2017/23984,2017,A1 .Location in patent: Paragraph 0680

47
[ 271-34-1 ]
[ 60290-21-3 ]

Reference： [1]Patent: WO2017/23987,2017,A1
[2]Patent: WO2017/24003,2017,A1
[3]Patent: WO2017/24010,2017,A1
[4]Patent: WO2017/23984,2017,A1

48
1-(phenylsulfonyl)-1H-pyrrolo[3,2-c]pyridine-5-oxide [ No CAS ]
[ 60290-21-3 ]

Reference： [1]Patent: WO2017/23987,2017,A1
[2]Patent: WO2017/24003,2017,A1
[3]Patent: WO2017/24010,2017,A1
[4]Patent: WO2017/23984,2017,A1

49
4-methoxy-3-[3-(pyrrolidin-1-yl)propoxy]aniline [ No CAS ]
[ 60290-21-3 ]
N-[4-methoxy-3-[3-(pyrrolidin-1-yl)propoxy]phenyl]-1H-pyrrolo[3,2-c]pyridin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; caesium carbonate; In 1,4-dioxane; at 100℃; for 12h;Inert atmosphere;	Into a 20-mL vial, was placed dioxane (2 mL), 4-chloro-lH-pyrrolo[3,2-c]pyridine (200 mg, 1.31 mmol, 1 equiv), 4-methoxy-3-[3-(pyrrolidin-l-yl)propoxy]aniline (329 mg, 1.31 mmol, 1 equiv), Brettphos (230 mg), Cs2CO3 (781 mg, 2.40 mmol, 1.83 equiv). The vial was purged and maintained with N2.The resulting solution was stirred for 12 h at 100C. The resulting mixture was concentrated under vacuum. The crude product was purified by Chiral-Prep-HPLC D TFA. This resulted in 74.1 mg (12%) of N-(4-methoxy-3-(3- (pyrrolidin-l-yl)propoxy)phenyl)-lH-pyrrolo[3,2-c]pyridin-4-amine as a an solid.

Reference： [1]Patent: WO2017/181177,2017,A1 .Location in patent: Paragraph 0651-0653

50
[ 60290-21-3 ]
N-((6-amino-2,4-dimethylpyridin-3-yl)methyl)-1-((3-chloroquinolin-6-yl)methyl)-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

51
[ 60290-21-3 ]
N-((6-amino-2,4-dimethylpyridin-3-yl)methyl)-1-((3-chloroquinolin-6-yl)methyl)-4-cyano-1H-pyrrolo[3,2-c]pyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

52
[ 60290-21-3 ]
3-chloro-6-((4-chloro-3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)methyl)quinoline [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

53
[ 60290-21-3 ]
methyl 4-chloro-1-((3-chloroquinolin-6-yl)methyl)-1H-pyrrolo[3,2-c]pyridine-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

54
[ 60290-21-3 ]
1-((3-chloroquinolin-6-yl)methyl)-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

55
[ 60290-21-3 ]
3-iodo-1H-pyrrolo[3,2-c]pyridine-4-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

56
[ 60290-21-3 ]
1-((3-chloroquinolin-6-yl)methyl)-3-iodo-1H-pyrrolo[3,2-c]pyridine-4-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

57
[ 60290-21-3 ]
methyl 1-((3-chloroquinolin-6-yl)methyl)-4-cyano-1H-pyrrolo[3,2-c]pyridine-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

58
[ 60290-21-3 ]
1-((3-chloroquinolin-6-yl)methyl)-4-cyano-1H-pyrrolo[3,2-c]pyridine-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2018/11628,2018,A1

59
[ 13154-24-0 ]
[ 60290-21-3 ]
4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		To a solution of 4- chloro-lH-pyrrolo[3,2-c]pyridine (150 mg, 0.98 mmol) in THF (10 mL) at -78 C was added 2.5 N ft-BuLi (0.6 mL, 1.5 mmol) and the reaction was stirred at -78 C for 30 min.Chlorotriisopropylsilane (284 mg, 1.47 mmol) was added and the mixture was stirred at -78 C for an additional 2 h. Water (400 mu,) was added followed by THF (20 mL) and the mixture was dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified via silica gel chromatography (0 - 40% acetone in petroleum ether) to afford the title compound (150 mg, 49% yield) as a colorless oil.MS (ES+) C16H25CIN2S1 requires: 308, found: 309 [M+H]+.

Reference： [1]Patent: WO2018/218197,2018,A2 .Location in patent: Paragraph 0417; 0418

60
[ 60290-21-3 ]
(R)-7-methyl-4-(1-(methylsulfonyl)piperidin-4-yl)-6-(1-(triisopropylsilyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine [ No CAS ]

Reference： [1]Patent: WO2018/218197,2018,A2

61
[ 60290-21-3 ]
(R)-7-methyl-4-(1-(methylsulfonyl)piperidin-4-yl)-6-(1H-pyrrolo[3,2-c]pyridin-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine [ No CAS ]

Reference： [1]Patent: WO2018/218197,2018,A2

62
[ 60290-21-3 ]
5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-1-[(3,4-dichlorophenyl)methyl]pyrrolo[3,2-c]pyridin-4-one [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

63
[ 60290-21-3 ]
1-[(3,4-dichlorophenyl)methyl]-5-[2-hydroxyethyl]pyrrolo[3,2-c]pyridin-4-one [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

64
[ 60290-21-3 ]
N-[2-[1-[(3,4-dichlorophenyl)methyl]-4-oxopyrrolo[3,2-c]pyridin-5-yl]ethyl]-N-methyl-4-nitrobenzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

65
[ 60290-21-3 ]
1-[(3,4-dichlorophenyl)methyl]-5-[2-(methylamino)ethyl]pyrrolo[3,2-c]pyridin-4-one [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

66
[ 60290-21-3 ]
1-[(3,4-dichlorophenyl)methyl]-5-(1-methyl-2-nitroethyl)pyrrolo[3,2-c]pyridin-4-one [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

67
[ 60290-21-3 ]
5-(2-amino-1-methylethyl)-1-[(3,4-dichlorophenyl)methyl]pyrrolo[3,2-c]pyridin-4-one [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

68
[ 60290-21-3 ]
1-[(3,4-dichlorophenyl)methyl]-5-[2-(dimethylamino)ethyl]pyrrolo[3,2-c]pyridin-4-one [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

69
[ 60290-21-3 ]
1-[(3,4-dichlorophenyl)methyl]-4-methoxypyrrolo[3,2-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1

70
[ 60290-21-3 ]
(2R)-2-[1-[(3,4-dichlorophenyl)methyl]-4-oxo-pyrrolo[3,2-c]pyridin-5-yl]propanoic acid [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

71
[ 60290-21-3 ]
1-[(3,4-dichlorophenyl)methyl]-5-[(1R)-2-hydroxy-1-methylethyl]pyrrolo[3,2-c]pyridin-4-one [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

72
[ 60290-21-3 ]
N-[(2R)-2-[1-[(3,4-dichlorophenyl)methyl]-4-oxopyrrolo[3,2-c]pyridin-5-yl]propyl]-N-methyl-4-nitrobenzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

73
[ 60290-21-3 ]
1-[(3,4-dichlorophenyl)methyl]-5H-pyrrolo[3,2-c]pyridin-4-one [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

74
[ 60290-21-3 ]
1-[(3,4-dichlorophenyl)methyl]-5-[(1R)-1-methyl-2-(methylamino)ethyl]pyrrolo[3,2-c]pyridin-4-one [ No CAS ]

Reference： [1]Patent: WO2019/106368,2019,A1
[2]Patent: WO2019/106368,2019,A1

75
[ 18880-04-1 ]
[ 60290-21-3 ]
4-chloro-1-[(3,4-dichlorophenyl)methyl]pyrrolo[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		A solution of 4-chloro-1 H-pyrrolo[3,2-c]pyridine (9.85 g, 0.065 mmol.) in anhydrous N,N-dimethylformamide (250 ml.) was cooled to 0C, before adding sodium hydride (60% in oil, 2.85 g, 0.071 mmol.) portion-wise over 10 minutes. The reaction mixture was stirred at 0C for 5 minutes, then at room temperature for 30 minutes. It was again cooled to 0C before adding 3,4-dichlorobenzyl bromide (10.3 mL, 0.071 mmol.) in N,N- dimethylformamide (20 mL). The reaction mixture was warmed to room temperature and stirred for 2.5 hours. (0335) [00145] The reaction mixture was treated with saturated aqueous ammonium chloride solution and then extracted with ethyl acetate (2x). The extract was washed with brine (3x) and then dried over magnesium sulfate, filtered and evaporated to give a colourless gum. The gum was purified on a silica column, eluting with 30% ethyl acetate, 70% iso- hexane and then dried under vacuum to give the title product as a white solid (16.9 g, 83%). H NMR (CDCI. ppm) d 8.07 (d, 1 H, J = 5.7 Hz), 7.39 (d, 1 H, J = 8.2 Hz), 7.19 (d, 1 H, J = 2.1 Hz), 7.16 (d, 1 H, J = 3.3 Hz), 7.05 (dd, 1 H, J = 5.8, 0.8 Hz), 6.88 (dd, 1 H, J = 8.3, 2.1 Hz), 6.72 (dd, 1 H, J = 3.3, 0.8 Hz), 5.27 (s, 2H). LCMS (m/z) [M+H] 31 1 , 313, 315.

Reference： [1]Patent: WO2019/106368,2019,A1 .Location in patent: Paragraph 00141-00145

76
[ 303963-93-1 ]
[ 60290-21-3 ]
1-((3aS,4R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-4-chloro-1H-pyrrolo[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45.6%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 25℃; for 16.0833h;	To a stirred solution of (3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2- dimethyl-3a,6a-dihydro-4H-cyclo penta[d] [l,3]dioxol-4-ol (0.5 g, 1.178 mmol) in THF (7 ml) at 0C was added 4-chloro-lH-pyrrolo [3,2-c] pyridine (0.305 g, 2.002 mmol), triphenylphosphine (1.081 g, 4.12 mmol) and DIAD (0.801 ml, 4.12 mmol) slowly and stirred for 5min. The reaction mixture was stirred at 25C for l6h. Volatiles were removed in vacuo and the crude residue was purified by combiflash (Rf200, Teledyne/Isco) instrument onto a redisep Rf column with gradient elution (0 to 10%) of ethyl acetate in petroleum ether to afford the title compound (0.3g, 45.6%) as an off-white solid. LCMS m/z = 559.23 (M+; 100).

Reference： [1]Patent: WO2019/116302,2019,A1 .Location in patent: Page/Page column 87

77
[ 60290-21-3 ]
tert-butyl 2-(4-chloro-3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)acetate [ No CAS ]

Reference： [1]Patent: WO2019/153080,2019,A1

78
[ 60290-21-3 ]
2-(3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridin-1-yl)acetic acid [ No CAS ]

Reference： [1]Patent: WO2019/153080,2019,A1

79
[ 60290-21-3 ]
ethyl 2-(3-iodo-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-1-yl)acetate [ No CAS ]

Reference： [1]Patent: WO2019/153080,2019,A1
[2]Patent: WO2019/153080,2019,A1

80
[ 60290-21-3 ]
ethyl 2-(4-hydroxy-3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)acetate [ No CAS ]

Reference： [1]Patent: WO2019/153080,2019,A1

81
[ 60290-21-3 ]
ethyl 2-(3-iodo-5-methyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-1-yl)acetate [ No CAS ]

Reference： [1]Patent: WO2019/153080,2019,A1
[2]Patent: WO2019/153080,2019,A1

82
[ 89031-84-5 ]
[ 60290-21-3 ]
C₁₆H₂₅ClN₂OSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.7%		To a solution of 4-chloro-lH-pyrrolo-[3,2-c]-pyridine [60290-21-3] (1.0 g, 6.5 mmol) dissolved in DMF (51 mL) at 0C was added portionwise sodium hydride (288 mg, 7.2 mmol). The reaction mixture was allowed to reach rt and stirred 45 min, after which it was re-cooled to 0C and (3-bromopropoxy)-tert-butyldimethylsilane [89031-84-5] (2.5 g, 9.8 mmol) was added dropwise. The mixture was then allowed to reach rt and stirred overnight. NaHCCh sat solution was added and the aqueous phase was extracted with EtOAcThe combined organic extracts were washed with water and brine, then dried over MgS04 and concentrated in vacuo to afford. The residue was purified by column chromatography (silica gel; DCM/MeOH, gradient from 100/0 to 95/5)) to yield 1-31 (2.7 g, 98.7%) as a yellow liquid.

Reference： [1]Patent: WO2019/243535,2019,A1 .Location in patent: Page/Page column 38-39

83
[ 86864-60-0 ]
[ 60290-21-3 ]
C₁₅H₂₃ClN₂OSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		4-Chloro-lH-pyrrolo[3,2-c]pyridine [60290-21-3] (1.00 g, 6.55 mmol) was dissolved in DMF (52 mL). NaH (60% dispersion in mineral oil, 288 mg, 7.21 mmol) was added at 0 C and the reaction mixture was stirred at room temperature. When gas evolution stopped, (2-bromocthoxy)-/er/-butyldimcthylsilanc (2.1 mL, 9.83 mmol) was added at 0 C. The reaction mixture was stirred at room temperature for 3 h and quenched with water. The mixture was diluted with EtOAc. The aqueous layer was extracted with EtOAc (3 times). The combined organic layers were washed with brine, dried (MgS04), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica, DCM/MeOH, gradient from 100:0 to 98:2) to afford 1-97 (1.6 g, 79%).

Reference： [1]Patent: WO2019/243535,2019,A1 .Location in patent: Page/Page column 57

84
2-iodo-5-carbethoxyoxazole [ No CAS ]
[ 60290-21-3 ]
C₁₃H₁₀ClN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine; In toluene; at 20 - 110℃; for 18h;Inert atmosphere; Sealed tube;	K2C03 (362 mg, 2.62 mmol), Cul (49.9 mg, 0.26 mmol) and trans- N,N'- dimethylcyclo hexane- 1, 2-diamine (82.7 pL, 0.52 mmol) were added to solution of 4- chloro-lH-pyrrolo[3,2-c]pyridine [60290-21-3] (200 mg, 1.31 mmol) and 1-159 (420 mg, 1.57 mmol) in toluene (10 mL) in a sealed tube while N2 was bubbling. The reaction mixture was stirred at room temperature for 10 min and at 110 C for 18 h. The mixture was cooled to room temperature and partitioned between NaHCCh (sat., aq.) and EtOAc. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried (MgS04), filtered and concentrated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 85:15) to afford 1-160 (42 mg, 9%, 86% purity).

Reference： [1]Patent: WO2019/243535,2019,A1 .Location in patent: Page/Page column 83

85
[ 96797-15-8 ]
[ 60290-21-3 ]
C₂₉H₂₁ClN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%		Cul (21.8 mg, 0.12 mmol), /nmv-N,N'-dimcthylcyclohcxanc- 1 ,2-diaminc (36.1 iiL, 0.23 mmol) and K2CO3 (317 mg, 2.29 mmol) were added to a solution of 1-169 (500 mg, 1.15 mmol) in toluene (6.25 mL) in a sealed tube while N2 was bubbling. After 10 min, 4-chloro-lH-pyrrolo[3,2-c]pyridine [60290-21-3] (227 mg, 1.15 mmol) was added. The reaction mixture was stirred at room temperature for 10 min, and at 100 C for 20 h. The reaction mixture was cooled to room temperature and diluted with NaHCCh (sat., aq.) and extracted with EtOAc. The organic layer was dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 80:20) to afford 1-170 (430 mg, 81%).

Reference： [1]Patent: WO2019/243535,2019,A1 .Location in patent: Page/Page column 87

86
[ 71759-87-0 ]
[ 60290-21-3 ]
C₁₂H₁₁ClN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine; In toluene; at 105℃; for 24h;	Cul (110 mg, 0.12 mmol), /rans-N, N?-dimethylcyclo hexane- 1, 2-diamine (37.9 iiL, 0.24 mmol) and K2C03 (332 mg, 2.40 mmol) were added to a stirred solution of 4- chloro-lH-pyrrolo[3,2-c]pyridine [60290-21-3] (238 mg, 1.56 mmol) and 4-iodo-l- methyl-lH-imidazole [71759-87-0] (250 mg, 1.20 mmol) in toluene (5 mL). The reaction mixture was stirred at 105 C for 24 h, cooled to room temperature and partitioned between NaHCCL (sat., aq.) and EtOAc. The aqueous phase was extracted with EtOAc (twice). The combined organic phases were washed with brine, dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 0:100) to afford 1-139 (120 mg, 43%).

Reference： [1]Patent: WO2019/243535,2019,A1 .Location in patent: Page/Page column 74-75

87
[ 19967-55-6 ]
[ 60290-21-3 ]
C₁₂H₁₃ClN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		NaH (60% dispersion in mineral oil, 220 mg, 5.50 mmol) was added to a solution of 4- chloro-5-azaindole [60290-21-3] (841 mg, 5.23 mmol) in DMF (30 mL). The reaction mixture was stirred at room temperature for 30 min under N2 atmosphere. l-Bromo-3- methyl-2-butanone [19967-55-6] (1.00 g, 5.76 mmol) was added dropwise and the reaction mixture was stirred for 16 h. The residue was dissolved with EtOAc and water. The organic layer was washed with water (twice) and brine, dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 90:10) to afford 1-149 (953 mg, 76%).

Reference： [1]Patent: WO2019/243535,2019,A1 .Location in patent: Page/Page column 78-79

88
[ 16681-56-4 ]
[ 60290-21-3 ]
C₁₀H₇ClN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; 2-(hydroxymethyl)-2-methylpropane-1,3-diol; caesium carbonate; In 1,4-dioxane; N,N-dimethyl-formamide; at 20 - 110℃; for 96h;Sealed tube; Inert atmosphere;	CS2CO3 (568 mg, 1.74 mmol) was added to a solution of Cul (16.2 mg, 85.1 pmol) and l,l,l-tris(hydroxymethyl)ethane (10.2 mg, 85.1 iimol) in anhydrous l,4-dioxane (45 mL) and anhydrous DMF (5 mL) in a sealed tube while N2 was bubbling. After 10 min, 4-chloro-lH-pyrrolo[3,2-c]pyridine [60290-21-3] (130 mg, 0.85 mmol) and 2-bromo- lH-imidazole [16681-56-4] (150 mg, 1.02 mmol) were added. The reaction mixture was stirred at room temperature for 10 min, and at 110 C for 4 days. The mixture was filtered through Celite and the solvents were evaporated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 60:40) to afford 1-151 (36 mg, 18%, 35% purity).

Reference： [1]Patent: WO2019/243535,2019,A1 .Location in patent: Page/Page column 80

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
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. 60290-21-3 ] {[proInfo.proName]}

Quality Control of [ 60290-21-3 ]

Related Doc. of [ 60290-21-3 ]

Product Details of [ 60290-21-3 ]

Calculated chemistry of [ 60290-21-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 60290-21-3 ]

Application In Synthesis of [ 60290-21-3 ]

[ 60290-21-3 ] Synthesis Path-Upstream 1~6

[ 60290-21-3 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 60290-21-3 ]

Chlorides

Related Parent Nucleus of [ 60290-21-3 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 60290-21-3 ]

Related Parent Nucleus of
[ 60290-21-3 ]