[ CAS No. 640735-23-5 ]

Name: 640735-23-5|4-Fluoro-7-azaindole|97%
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Quality Control of [ 640735-23-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 640735-23-5 ]

CAS No. :	640735-23-5	MDL No. :	MFCD08272231
Formula :	C₇H₅FN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	136.13 g/mol	Pubchem ID :	11297998
Synonyms :

Calculated chemistry of of [ 640735-23-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.05
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) :	-6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.39
Log Po/w (XLOGP3) :	1.41
Log Po/w (WLOGP) :	2.12
Log Po/w (MLOGP) :	1.42
Log Po/w (SILICOS-IT) :	2.5
Consensus Log Po/w :	1.77

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.24
Solubility :	0.786 mg/ml ; 0.00578 mol/l
Class :	Soluble
Log S (Ali) :	-1.62
Solubility :	3.29 mg/ml ; 0.0242 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.16
Solubility :	0.0944 mg/ml ; 0.000693 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.63

Safety of [ 640735-23-5 ]

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 [ 640735-23-5 ]

* 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 [ 640735-23-5 ]
Downstream synthetic route of [ 640735-23-5 ]

[ 640735-23-5 ] Synthesis Path-Upstream 1~11

1
[ 74420-00-1 ]
[ 74420-02-3 ]
[ 640735-23-5 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025

2
[ 640735-25-7 ]
[ 640735-23-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 1 h; Inert atmosphere	[0722] To a stirred solution of 4-fluoro-i-(triisopropylsilyl)-1H-pyrrolo [2,3-bj pyridine (3 g, 10 mmol) in THF (15 mL) at 0 °C under an argon atmosphere was added tetra butyl ammonium fluoride 1M in THF (10.5 mL). The reaction mixture was warmed to room temperature and stirred for 1 h. After consumption of starting material (by TLC), the reactionmixture was diluted with water (50 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 20percentEtOAc: Hexane to afford 4-fluoro-1H-pyrrolo [2,3-bj pyridine (1.3 g, 94percent) as an off-white solid. ‘H NMR (CDC13, 400 MHz): 10.52 (brs, 1H), 8.30-8.25 (m, 1H), 7.32-7.30 (m, 1H), 6.81 (dd, 1H), 6.59 (s, 1H); TLC: 20percent EtOAc Hexane (R 0.2).

Reference： [1] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025
[2] Tetrahedron Letters, 2007, vol. 48, # 9, p. 1527 - 1529
[3] Patent: WO2017/31325, 2017, A1, . Location in patent: Paragraph 0722

3
[ 74420-00-1 ]
[ 74420-02-3 ]
[ 640735-23-5 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025

4
[ 55052-28-3 ]
[ 640735-23-5 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 9, p. 1527 - 1529
[2] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025

5
[ 640735-22-4 ]
[ 640735-23-5 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025

6
[ 640735-24-6 ]
[ 640735-23-5 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 9, p. 1527 - 1529
[2] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025
[3] Patent: WO2017/31325, 2017, A1,

7
[ 55052-24-9 ]
[ 640735-23-5 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025
[2] Patent: WO2017/31325, 2017, A1,

8
[ 348640-06-2 ]
[ 640735-23-5 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025
[2] Patent: WO2017/31325, 2017, A1,

9
[ 319474-34-5 ]
[ 640735-23-5 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 9, p. 1527 - 1529

10
[ 920501-58-2 ]
[ 640735-23-5 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 9, p. 1527 - 1529

11
[ 271-63-6 ]
[ 640735-23-5 ]

Reference： [1] Patent: WO2017/31325, 2017, A1,

[ 640735-23-5 ] Synthesis Path-Downstream 1~31

1
[ 109-01-3 ]
[ 640735-23-5 ]
4-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 1527 - 1529

2
[ 31252-42-3 ]
[ 640735-23-5 ]
C₁₉H₂₁N₃ [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 1527 - 1529

3
[ 110-91-8 ]
[ 640735-23-5 ]
4-(morpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 1527 - 1529

4
[ 110-89-4 ]
[ 640735-23-5 ]
4-(1-piperidyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 1527 - 1529

5
[ 123-75-1 ]
[ 640735-23-5 ]
C₁₁H₁₃N₃ [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 1527 - 1529

6
[ 319474-34-5 ]
[ 640735-23-5 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 1527 - 1529

7
[ 920501-58-2 ]
[ 640735-23-5 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 1527 - 1529

8
[ 55052-28-3 ]
[ 640735-23-5 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 1527 - 1529
[2]Organic Letters,2003,vol. 5,p. 5023 - 5025

9
[ 640735-24-6 ]
[ 640735-23-5 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 1527 - 1529
[2]Organic Letters,2003,vol. 5,p. 5023 - 5025
[3]Patent: WO2017/31325,2017,A1

10
[ 55052-24-9 ]
[ 640735-23-5 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 5023 - 5025
[2]Patent: WO2017/31325,2017,A1

11
[ 348640-06-2 ]
[ 640735-23-5 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 5023 - 5025
[2]Patent: WO2017/31325,2017,A1

12
[ 640735-22-4 ]
[ 640735-23-5 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 5023 - 5025

13
[ 808144-32-3 ]
[ 640735-23-5 ]
[ 849068-01-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With aluminum (III) chloride; In dichloromethane; for 14h;	Example 44 2-(2, 3-DIFLUORO-PHENYL)-1-(4-FLUORO-LH-PYRROLO [2S3-B] PY ridin-3-yl)-ethanone [0256] 4-FLUORO-LH-PYRROLO [2, 3-B] PYRIDINE (230mg, 1. 69MMOL) (ORG. Lett. 2003,5 (26), 5023) and AlCl3 (678, 5. lmmol) in methylene chloride (30mL) were stirred for 0.5hr. To this mixture was added 2,3-Difluoro-phenyl)-acetyl chloride (644mg, 3. 38MMOL) and the reaction solution was stirred for 14HR. Quenched with methanol (50mL) and water (50mL) and extracted with ethyl acetate, dried (NA2SO4). Flash chromatography (methylene chloride/methanol) afforded 2- (2, 3-Difluoro-phenyl)-l- (4-fluoro-lH-pyrrolo [2, 3-B] PY ridin-3-yl)-ethanone (448mg, 91% YIELD). LC/MS : RT 3.16mins. ; m/e 287.1 (M+H), 285.2 (M-H).

Reference： [1]Patent: WO2005/28475,2005,A2 .Location in patent: Page/Page column 145-146

14
[ 640735-23-5 ]
[ 1172067-55-8 ]

Yield	Reaction Conditions	Operation in experiment
75.2%	With nitric acid; at 0℃; for 0.166667h;	00341] 4-Fluoro-lH-pyrrolo[2,3-b]pyridine (1.80 g, 13.2 mmol, prepared as described inThibault, et al. as cited in Scheme 1 above) was added slowly to fuming HNO3 at 00C and stirred for 10 minutes. Ice was then added, followed by the addition of water. The reaction was then filtered, and the solid product was washed with water and dried to give 4-fluoro-3-nitro-lH- pyrrolo[2,3-b]pyridine (1.80 g, 75.2% yield).

Reference： [1]Patent: WO2009/89352,2009,A1 .Location in patent: Page/Page column 81

15
[ 271-63-6 ]
[ 640735-23-5 ]

Reference： [1]Patent: WO2017/31325,2017,A1

16
[ 640735-23-5 ]
2-cyclopropyl-1-(4-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one [ No CAS ]

Reference： [1]Patent: WO2017/31325,2017,A1

17
[ 640735-23-5 ]
2-bromo-2-cyclopropyl-1-(4-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one [ No CAS ]

Reference： [1]Patent: WO2017/31325,2017,A1

18
[ 640735-23-5 ]
(Z)-N’-(1-cyclopropyl-2-(4-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-oxoethoxy)-6-methoxy-5-(4-methyl-1H-imidazol-1-yl)picolinimidamide [ No CAS ]

Reference： [1]Patent: WO2017/31325,2017,A1

19
[ 640735-23-5 ]
6-cyclopropyl-5-(4-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-5,6-dihydro-4H-1,2,4-oxadiazine [ No CAS ]

Reference： [1]Patent: WO2017/31325,2017,A1

20
[ 640735-23-5 ]
(+)-6-cyclopropyl-5-(4-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-5,6-dihydro-4H-1,2,4-oxadiazine [ No CAS ]
(-)-6-cyclopropyl-5-(4-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-5,6-dihydro-4H-1,2,4-oxadiazine [ No CAS ]

Reference： [1]Patent: WO2017/31325,2017,A1

21
[ 74-88-4 ]
[ 640735-23-5 ]
4-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 12h;Inert atmosphere;	[0723] To a stirred solution of 4-fluoro-1H-pyrrolo [2,3-bj pyridine (1.4 g, 10 mmol) in DMF (42 mL) at 0 C under an argon atmosphere were added potassium carbonate (2.1 g, 15 mmol) and methyl iodide (1.75 g, 12 mmol). The reaction mixture was warmed to room temperature and stirred for 12 h. After consumption of starting material (by TLC), the reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 15%EtOAc:Hexane to afford 4-fluoro-1-methyl-1H-pyrrolo [2,3-bj pyridine (700 mg, 45%) as pale brown liquid. ?H NMR (CDC13, 400 MHz): 8.26 (dd, 1H), 7.12 (d, 1H), 6.78 (dd, 1H), 6.51 (d, 1H), 3.90 (s, 3H); TLC: 20% EtOAc Hexane (Rj: 0.5).

Reference： [1]Patent: WO2017/31325,2017,A1 .Location in patent: Paragraph 0723

22
[ 640735-23-5 ]
4-fluoro-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 714 - 722

23
[ 640735-23-5 ]
2-[[4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridin-1-yl]methoxy]ethyltrimethylsilane [ No CAS ]