849067-90-9|1H-Pyrrolo[2,3-b]pyridine-5-carbaldehyde| Ambeed

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Quality Control of [ 849067-90-9 ] Purity: 98% SDS Specification

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Product Details of [ 849067-90-9 ]

CAS No. :	849067-90-9
Formula :	C₈H₆N₂O
M.W :	146.15
SMILES Code :	O=CC1=CC2=C(NC=C2)N=C1
MDL No. :	MFCD08272241
InChI Key :	HDANOCTXZFZIHB-UHFFFAOYSA-N
Pubchem ID :	22832051

Safety of [ 849067-90-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 849067-90-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	41.48
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	45.75 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.02
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.77
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.38
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.35
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.17
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.14

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.77
Solubility	2.48 mg/ml ; 0.017 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.31
Solubility	7.14 mg/ml ; 0.0489 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.84
Solubility	0.213 mg/ml ; 0.00146 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.64 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.16

Application In Synthesis of [ 849067-90-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 849067-90-9 ]

[ 849067-90-9 ] Synthesis Path-Downstream 1~30

1
[ 849067-90-9 ]
[ 506-59-2 ]
[ 849067-91-0 ]

Yield	Reaction Conditions	Operation in experiment
33%	With sodium hydroxide; sodium cyanoborohydride; In methanol; for 12h;	Example 34 Step B: DIMETHYL- (LH-PYRROLO [2, 3-B] PYRIDIN-5-YLMETHYL)-AMINE [0240] To 1H-Pyrrolo [2, 3-b] pyridine-5-carbaldehyde (114mg, 0.78mmol), in methanol (lOmL) was added dimethylamine hydrochloride (127mg, 1.56mmol, NaOH (31.2 mg, 0. 78MMOL), sodium cyanoborohydride (49mg, 0.78mmol) and the solution was stirred under nitrogen for 12 hr. Poured into water (50mL), extracted with ethyl acetate, dried (NA2SO4) to afforded Dimethyl- (LH-PYRROLO [2, 3-b] pyridin-5-ylmethyl)-amine (44mg, 33percent yield) used without purification. MS: m/e 176.1 (M+H).

References: [1]Patent: WO2005/28475,2005,A2 .Location in patent: Page/Page column 137-138.

2
C₇H₅LiN₂ [ No CAS ]
[ 149-73-5 ]
[ 849067-90-9 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; hexanes; at -78 - 23℃;	Example 33 Step A: LN-PYRROLO [2, 3-B] PYRIDINE-5-CARBALDEHYDE [0238] To 5-BROMO-LH-PYRROLO [2, 3-b] pyridine (1.5g, 7. 61mmol) in THF (200 mL) at-78 C, under nitrogen, was 'added n-butyl lithium (2.5M in hexanes, 15.2 mmol, 6.1 mL), and the reaction solution was stirred with an overhead motor. After LHR, the resulting orange gel was quenched with methyformate (4.56g, 76mmol) and the reaction solution was allowed to slowly warm to 23C. The solution was poured into water and extracted with ethyl acetate, dried (Na2SO4) to give 1H-PYRROLO [2, 3-b] PYRIDINE-5-CARBALDEHYDE (0. 68G, 61percent yield) as a yellow solid. [0239] 1H-NMR (DMSO-d6,500 MHz) 8 : 12.17 (1H, bs), 10. 09 (LH, s), 8. 77-8.76 (1H, d), 8. 49-8. 48 (1H, D), 7.65-7. 64 (1H, d), 6.68-6. 67 (LH, D). LC/MS: Rt 2. 18mins. ; m/e 146.9 (M+H), 144.9 (M-H).

References: [1]Patent: WO2005/28475,2005,A2 .Location in patent: Page/Page column 137.

3
[ 849067-97-6 ]
[ 849067-90-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridinium chlorochromate; In dichloromethane; at 20℃;	B. lH-Pyrrolo[2,3-b]pyridine-5-carbaldehyde.; (1H-Pyrrolo[2,3- b]pyridin-5-yl)methanol (crude from previous reaction) was dissolved in anhydrous methylenechloride (50 mL). Pyridiniumchlorochromate (3.70 g, 17.0 mmol) was added to the solution and stirred at room temperature overnight. The reaction mixture was filtered through silica gel and washed with ethyl acetate. Organics were poured into water (150 mL), extracted with EtOAc (4x100 mL), combined organic layers were dried with sodium sulfate, and concentrated under reduced pressure to afford the title compound (0.72 g, 4.93 mmol, 87percent over 2 steps) as a white solid. MS (ESI) m/z 147.1 [M+ 1]+.

References: [1]Patent: WO2008/51494,2008,A1 .Location in patent: Page/Page column 166.

4
[ 849067-90-9 ]
[ 624-31-7 ]
[ 1196079-52-3 ]

References: [1]Chemical Communications,2012,vol. 48,p. 4253 - 4255.
[2]Green Chemistry,2012,vol. 14,p. 2314 - 2320.

5
[ 849067-90-9 ]
[ 624-31-7 ]
[ 1373516-14-3 ]

References: [1]Chemical Communications,2012,vol. 48,p. 4253 - 4255.
[2]Green Chemistry,2012,vol. 14,p. 2314 - 2320.

6
[ 849067-90-9 ]
[ 98-59-9 ]
[ 1445856-01-8 ]

Yield	Reaction Conditions	Operation in experiment
56%		step2: To a solution of lH-pyrrolo[2,3-6]pyridine-5-carbaldehyde (500 mg, 3.42 mmol) in THF (50 mL) at 0 °C was added NaH (205 mg, 60percent in oil, 5.13 mmol) with vigorous stirring. After 30 min, TsCl (845 mg, 4.45 mmol) was added. The reaction mixture was stirred at RT for 18 h, and then the solvent was removed in vacuo. The residue was partitioned between DCM (300 mL) and water (100 mL). The organic layer was separated, dried (MgSO i), filtered, and concentrated to afford 580 mg (56percent) of 1-tosyl- lH-pyrrolo[2,3- yridine-5-carbaldehyde as yellow solid. MS (ESI) m/z: 301.2 [M+l]+.

References: [1]Patent: WO2013/92940,2013,A1 .Location in patent: Page/Page column 40.

7
[ 849067-90-9 ]
[ 1445856-02-9 ]

References: [1]Patent: WO2013/92940,2013,A1 .

8
[ 849067-90-9 ]
[ 1445856-00-7 ]

References: [1]Patent: WO2013/92940,2013,A1 .

9
[ 107-31-3 ]
[ 183208-35-7 ]
[ 849067-90-9 ]

Yield	Reaction Conditions	Operation in experiment
33%		step 1 : To a solution of 5-bromo-1H-pyrrolo[2,3-6]pyridine (2.0 g, 10 mmol) in anhydrous THF (50 mL) at -70 °C under nitrogen was added n-butyl lithium (2.5 M in hexane, 50 mmol) and the reaction mixture was stirred for 1 h at -70 °C. The resulting orange gel was quenched with methyl formate (10 mL) and the reaction mixture was slowly warmed to RT. The mixture was poured into water (20 mL) and extracted with EtOAc (2 x 250 mL). The organic layers were combined, dried (Na2SO4), filtered, and concentrated to afford 500 mg, (33percent) of 1H-pyrrolo[2,3-6]pyridine-5-carbaldehyde as yellow solid. MS (ESI) m/z: 147.2 [M+l] +.

References: [1]Patent: WO2013/92940,2013,A1 .Location in patent: Page/Page column 40.

10
[ 849067-90-9 ]
N-((1H-pyrrolo[2,3-b]pyridin-5-yl)methyl)-5-(4-((2-oxopyridin-1(2H)-yl)methyl)benzyl)nicotinamide [ No CAS ]

References: [1]Patent: WO2015/103317,2015,A1 .

11
[ 849067-90-9 ]
[ 849067-97-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With methanol; sodium tetrahydroborate; for 1h;	To the solution of lH-pyrrolo[2,3-b]pyridine-5-carbaldehyde (400 mg, 2.73 mmol, 1.0 eq) in MeOH (10 mL) was added sodium borohydride (208 mg, 5.46 mmol, 2.0 eq). The reaction was stirred for 1 h, and then purified via flash chromatography to afford (lH-pyrrolo[2,3-b]pyridin-5-yl)methanol as a white solid (310 mg, 76percent).

References: [1]Patent: WO2015/103317,2015,A1 .Location in patent: Page/Page column 175.

12
[ 849067-90-9 ]
5-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

References: [1]Patent: WO2015/103317,2015,A1 .

13
[ 849067-90-9 ]
(1H-pyrrolo[2,3-b]pyridin-5-yl)methanamine dihydrochloride [ No CAS ]

References: [1]Patent: WO2015/103317,2015,A1 .

14
[ 849067-90-9 ]
N-((3-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)methyl)-5-(4-((2-oxopyridin-1(2H)-yl)methyl)benzyl)nicotinamide [ No CAS ]

References: [1]Patent: WO2015/103317,2015,A1 .

15
[ 68-12-2 ]
[ 183208-35-7 ]
[ 849067-90-9 ]

Yield	Reaction Conditions	Operation in experiment
69%		1H-Pyrrolo[2,3-b]pyridine-5-carbaldehyde To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (1.0 g, 5.0 mmol, 1.0 eq.) in anhydrous THF (50 mL) at -78° C. under argon was slowly added a solution of 1.6 M n-butyl lithium in hexane (6.7 mL, 10.7 mmol, 2.1 eq.) and the reaction mixture was allowed to stir for next 40 min at -78° C. To the resulting suspension 1 mL of dry DMF was added successively and the reaction mixture stirring was continued at rt overnight. Then the reaction mixture was quenched with saturated solution of NH4Cl; the organic layer was separated and the aqueous phase was extracted with EtOAc. The organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated to afford 1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (Intermediate 3a) as an yellow solid (1.0 g; yield: 69percent; UPLC purity: 98percent).
		1. To a solution of 5-bromo-lH-pyrrolo[2,3-b]pyridine (600 mg, 3.045 mmol) in 20 mL of THF, was added sodium hydride (60 wt dispersion, 146 mg, 3.65 mmol) at 0 °C. After 30 min, the reaction was added 4.38 mL of n-BuLi solution in hexanes (1.6 M) at -15 °C. After 1 hr at -15 °C, DMF (10 mL) was added and allowed to warm to RT. After 2 hr, the reaction was quenched with water, and extracted with EtOAc (x3). The combined organic extracts were washed with water (x2), dried (MgS04), and concentrated to give crude 1 H-pyrrolo [2, 3- b]pyridine-5-carbaldehyde (572.8 mg ).

References: [1]Patent: US2018/179199,2018,A1 .Location in patent: Paragraph 0459-0460.
[2]Patent: WO2016/114816,2016,A1 .Location in patent: Paragraph 0300.

16
[ 849067-90-9 ]
(5-methoxy-1H-indol-2-yl)(1H-pyrrolo[2,3-b]pyridin-5-yl)methanone [ No CAS ]

References: [1]Patent: WO2016/114816,2016,A1 .

17
[ 849067-90-9 ]
(5-methoxy-1-(phenylsulfonyl)-1H-indol-2-yl)(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol [ No CAS ]

References: [1]Patent: WO2016/114816,2016,A1 .

18
[ 849067-90-9 ]
(5-methoxy-1-(phenylsulfonyl)-1H-indol-2-yl)(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)methanone [ No CAS ]

References: [1]Patent: WO2016/114816,2016,A1 .

19
[ 849067-90-9 ]
[ 98-09-9 ]
1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		To solution of crude lH-pyrrolo[2,3-b]pyridine-5-carbaldehyde (572.8 mg, 3.92 mmol) in 30 mL of THF, was added sodium hydride (60 wt dispersion, 314 mg, 7.84 mmol) at 0 °C. After 1.5 hr at RT, phenylsulfonylchloride (1.0 mL, 7.84 mmol) was added. After 2hr, the reaction was quenched with saturated ammonium chloride solution at 0 °C, and extracted with EtOAc (x3). The combined organic extracts were dried (MgS04), filtered, and concentrated. Flash chromatography (35percent EtOAc/Hexanes) gave 1 -(phenylsulfonyl)- lH-pyrrolo[2, 3- b]pyridine-5-carbaldehyde (381 mg, 34percent). *H NMR (400 MHz, CDC13) delta ppm: 10.13 (s, IH), 8.90 (s, IH), 8.36 (s, IH), 8.24 (d, J=8.0 Hz, 2H), 7.86 (d, J=4.0 Hz, IH), 7.62 (t, J=7.6 Hz, IH), 7.52 (t, J=8.0 Hz, 2H), 6.73 (d, J=4.0 Hz, IH).

References: [1]Patent: WO2016/114816,2016,A1 .Location in patent: Paragraph 0301.

20
[ 849067-90-9 ]
[ 1576-35-8 ]
[ 1357586-18-5 ]