[ CAS No. 1111638-02-8 ] {[proInfo.proName]}

Name: 1111638-02-8|5-Bromo-2-methyl-7-azaindole|97%
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SKU: A186669
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Quality Control of [ 1111638-02-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1111638-02-8 ]

CAS No. :	1111638-02-8	MDL No. :	MFCD15529124
Formula :	C₈H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IWLFWGLFINYFHA-UHFFFAOYSA-N
M.W :	211.06	Pubchem ID :	45489691
Synonyms :

Calculated chemistry of [ 1111638-02-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.76
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) :	-5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.97
Log Po/w (XLOGP3) :	2.4
Log Po/w (WLOGP) :	2.63
Log Po/w (MLOGP) :	2.06
Log Po/w (SILICOS-IT) :	3.15
Consensus Log Po/w :	2.44

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.27
Solubility :	0.114 mg/ml ; 0.000542 mol/l
Class :	Soluble
Log S (Ali) :	-2.64
Solubility :	0.479 mg/ml ; 0.00227 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.16
Solubility :	0.0147 mg/ml ; 0.0000697 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.5

Safety of [ 1111638-02-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1111638-02-8 ]

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

Upstream synthesis route of [ 1111638-02-8 ]
Downstream synthetic route of [ 1111638-02-8 ]

[ 1111638-02-8 ] Synthesis Path-Upstream 1~6

1
[ 1111638-01-7 ]
[ 1111638-02-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydroxide In methanol for 2 h; Reflux	Preparation of Method A Intermediate 4: 5-Bromo-2-methyl-lH-pyrrolo [2,3-6] pyridine[0427] Starting material 3 (88 mg, 0.251 mmol) is dissolved in MeOH (4 ml), 2 N NaOH (1 ml) is added and the mixture is refluxed for 2 h. EtOAc is added and the organic phase is washed with 1 N NaOH and water. After purification by silica gel chromatography (slow gradient from 0 to 2percent MeOH in DCM), 40 mg (0.19 mmol, 76percent) of 4 is obtained. 1H NMR (CDCls, 300 MHz): δ 10.26 (bs, 1H), 8.22 (d, J= 2.1 Hz, 1H), 8.92 (d, J= 2.1 Hz, 1H), 6.13 (s, 1H), 2.52 (s, 3H). MS (m/z): 210 (M+H).
76%	With sodium hydroxide In methanol for 2 h; Reflux	Starting material 3 (88 mg, 0.251 mmol) is dissolved in MeOH (4 ml), 2 N NaOH (1 ml) is added and the mixture is refluxed for 2 h. EtOAc is added and the organic phase is washed with 1 N NaOH and water. After purification by silica gel chromatography (slow gradient from 0 to 2percent MeOH in DCM), 40 mg (0.19 mmol, 76percent) of 4 is obtained. NMR (CDCI₃, 300 MHz): δ 10.26 (bs, 1H), 8.22 (d, J= 2.1 Hz, 1H), 8.92 (d, J= 2.1 Hz, 1H), 6.13 (s, 1H), 2.52 (s, 3H). MS (m/z): 210 (M+H).
76.9%	With sodium hydroxide In methanol; water at 65℃; for 2 h; Inert atmosphere	To a solution of compound 19 (1.3 g, 3.7 mmol) in Methynol (MeOH, 85 mL) 2 M of Sodium hydroxide (NaOH) solution (22 mL) was added. After refluxing for 2 h, the mixture was extracted with EtOAc (100 mL * 3). The organic phase was washed with brine (30 mL * 2), dried over Na₂SO₄, concentrated to give compound 20 as a white solid (600 mg, 76.9percent yield). ¹H NMR (400 MHz, DMSO-d₆) δ 11.69 (s, 1H, NH), 8.13 (s, 1H, Ar-H), 8.01 (s, 1H, Ar-H), 6.14 (s, 1H, Ar-H), 2.40 (s, 3H, CH3). ESI-MS m/z: 211.16, 213.16 (M+H)⁺.

50.2%

With sodium hydroxide; water In tetrahydrofuran at 20℃; Heating / reflux

Preparation of 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (B-7-6)^Br VVλ_ aq. NaOH "'V^{^}VA kN^N THF ' ^/VBs ^HB-7-5 B-7-6To a suspension of 5-bromo-1-(4-bromophenylsulfonyl)-2-methyl-1 H-pyrrolo[2,3-b]pyridine (B-7-5) (4 g, 11.4 mmol) in THF (20 mL) was added aq. NaOH (20 mL) at room temperature. The mixture was heated to reflux overnight. LC-MS showed the reaction was complete. Water (100 mL) and EtOAc (50 mL^χ3) were added into the mixture. The organic layer was separated, dried over anhydrous Na₂SO₄ and concentrated to give crude mixture which was purified via prep. HPLC to afford 5-bromo-2-methyl-1 H- pyrrolo[2,3-b]pyridine (B-7-6) (1.2 g, 50.2percent) as a white solid.

Reference： [1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 582 - 586
[2] Patent: WO2011/149950, 2011, A2, . Location in patent: Page/Page column 151-152
[3] Patent: WO2014/85795, 2014, A1, . Location in patent: Paragraph 0394
[4] Bioorganic Chemistry, 2016, vol. 65, p. 146 - 158
[5] Patent: WO2009/16460, 2009, A2, . Location in patent: Page/Page column 74

2
[ 1312755-43-3 ]
[ 1111638-02-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 85℃; for 1 h;	Step 3 : 5-Bromo-2-methyl-lH-pyrrolor2,3-b1pyridine5-Bromo-3-prop-l-ynyl-pyridin-2-ylamine (91 g, 431 mmol) was treated with a 1M solution of potassium ie/t-butoxide in ie/t-butanol (700 mL) and the reaction mixture was heated at 85 °C for 1 hour. The mixture was then allowed to cool to ambient temperature and poured onto a 1: 1 mixture of water / ice {ca. 1 L). The resultant precipitate was collected by filtration, washed with water and left to air dry. The resultant solid was dissolved in dichloromethane, dried (Na₂S0₄) and evaporated then triturated with diethyl ether to afford the title compound as a brown solid (88.7 g, 97percent). NMR (400 MHz, CDC1₃): 10.21 (s, 1H), 8.22 (d, J = 2.1 Hz, 1H), 7.91 (d, J = 2.1 Hz, 1H), 6.13 (s, 1H),2.52 (s, 3H).
90%	With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 85℃; for 20 h;	A mixture of 5-bromo-3-prop-i-ynyl-pyridin-2-amine (646 mg, 3.06 mmol), potassium tert-butoxide (558 mg, 4.97 mmol) and 2-methyl-2-propanol (10 mL) was stirred at 85 °C for 20 h. The reaction was diluted with water (30 mL), extracted with ethyl acetate (50 mL x3), dried over Na2504, filtered and concentrated to give 5-bromo-2-methyl-1H-pyrrolo[2,3- b]pyridine (584 mg, 90percent). LCMS (ESI) [M+H] = 211.0.

Reference： [1] Patent: WO2011/73263, 2011, A1, . Location in patent: Page/Page column 79
[2] Patent: WO2018/167147, 2018, A1, . Location in patent: Paragraph 0209; 0210

3
[ 183208-35-7 ]
[ 1111638-02-8 ]

Reference： [1] Patent: WO2011/149950, 2011, A2,
[2] Patent: WO2014/85795, 2014, A1,
[3] Bioorganic Chemistry, 2016, vol. 65, p. 146 - 158
[4] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 582 - 586

4
[ 1001070-33-2 ]
[ 1111638-02-8 ]

5
[ 381233-96-1 ]
[ 1111638-02-8 ]

Reference： [1] Patent: WO2011/73263, 2011, A1,
[2] Patent: WO2018/167147, 2018, A1,

6
[ 1072-97-5 ]
[ 1111638-02-8 ]

Reference： [1] Patent: WO2011/73263, 2011, A1,

[ 1111638-02-8 ] Synthesis Path-Downstream 1~73

1
[ 1111638-02-8 ]
[ 73183-34-3 ]
[ 1111638-03-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80℃;	Preparation of 2-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrolo[2,3-b]pyridine (B-7-7)B-7-7 <n="76"/>To a mixture of 5-bromo-2-methyl-1 H-pyrrolo[2,3-b]pyridine (B-7-6) (0.5 g, 2.4 mmol), bis(pinacolato)diboror) (1.2 g, 4.7 mmol) and KOAc (0.7 g, 7.1 mmol) in DMF (50 mL) was added Pd(dppf)2CI2 (0.05 g, 0.06 mmol). The mixture was degassed under N2 for 2 minutes. Then the mixture was stirred at 8O0C overnight. TLC (CH2CI2: MeOH = 20:1 ) showed that the reaction was complete. Water (50 mL) and EtOAc (50 mL><3) were added into the mixture. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated to give crude 2-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)-1 H-pyrrolo[2,3-b]pyridine (B-7-7) (1.8 g) as a brown solid.

Reference： [1]Patent: WO2009/16460,2009,A2 .Location in patent: Page/Page column 74-75

2
[ 1111638-01-7 ]
[ 1111638-02-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydroxide; In methanol; for 2h;Reflux;	Preparation of Method A Intermediate 4: 5-Bromo-2-methyl-lH-pyrrolo [2,3-6] pyridine[0427] Starting material 3 (88 mg, 0.251 mmol) is dissolved in MeOH (4 ml), 2 N NaOH (1 ml) is added and the mixture is refluxed for 2 h. EtOAc is added and the organic phase is washed with 1 N NaOH and water. After purification by silica gel chromatography (slow gradient from 0 to 2% MeOH in DCM), 40 mg (0.19 mmol, 76%) of 4 is obtained. 1H NMR (CDCls, 300 MHz): delta 10.26 (bs, 1H), 8.22 (d, J= 2.1 Hz, 1H), 8.92 (d, J= 2.1 Hz, 1H), 6.13 (s, 1H), 2.52 (s, 3H). MS (m/z): 210 (M+H).
76%	With sodium hydroxide; In methanol; for 2h;Reflux;	Starting material 3 (88 mg, 0.251 mmol) is dissolved in MeOH (4 ml), 2 N NaOH (1 ml) is added and the mixture is refluxed for 2 h. EtOAc is added and the organic phase is washed with 1 N NaOH and water. After purification by silica gel chromatography (slow gradient from 0 to 2% MeOH in DCM), 40 mg (0.19 mmol, 76%) of 4 is obtained. NMR (CDCI3, 300 MHz): delta 10.26 (bs, 1H), 8.22 (d, J= 2.1 Hz, 1H), 8.92 (d, J= 2.1 Hz, 1H), 6.13 (s, 1H), 2.52 (s, 3H). MS (m/z): 210 (M+H).
76.9%	With sodium hydroxide; In methanol; water; at 65℃; for 2h;Inert atmosphere;	To a solution of compound 19 (1.3 g, 3.7 mmol) in Methynol (MeOH, 85 mL) 2 M of Sodium hydroxide (NaOH) solution (22 mL) was added. After refluxing for 2 h, the mixture was extracted with EtOAc (100 mL * 3). The organic phase was washed with brine (30 mL * 2), dried over Na2SO4, concentrated to give compound 20 as a white solid (600 mg, 76.9% yield). 1H NMR (400 MHz, DMSO-d6) delta 11.69 (s, 1H, NH), 8.13 (s, 1H, Ar-H), 8.01 (s, 1H, Ar-H), 6.14 (s, 1H, Ar-H), 2.40 (s, 3H, CH3). ESI-MS m/z: 211.16, 213.16 (M+H)+.

50.2%

With sodium hydroxide; water; In tetrahydrofuran; at 20℃;Heating / reflux;

Preparation of 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (B-7-6)Br VVlambda_ aq. NaOH "'V^VA kN^N THF ' ^/VBs HB-7-5 B-7-6To a suspension of 5-bromo-1-(4-bromophenylsulfonyl)-2-methyl-1 H-pyrrolo[2,3-b]pyridine (B-7-5) (4 g, 11.4 mmol) in THF (20 mL) was added aq. NaOH (20 mL) at room temperature. The mixture was heated to reflux overnight. LC-MS showed the reaction was complete. Water (100 mL) and EtOAc (50 mLchi3) were added into the mixture. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated to give crude mixture which was purified via prep. HPLC to afford 5-bromo-2-methyl-1 H- pyrrolo[2,3-b]pyridine (B-7-6) (1.2 g, 50.2%) as a white solid.

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 582 - 586
[2]Patent: WO2011/149950,2011,A2 .Location in patent: Page/Page column 151-152
[3]Patent: WO2014/85795,2014,A1 .Location in patent: Paragraph 0394
[4]Bioorganic Chemistry,2016,vol. 65,p. 146 - 158
[5]Patent: WO2009/16460,2009,A2 .Location in patent: Page/Page column 74

3
[ 381233-96-1 ]
[ 1111638-02-8 ]

Reference： [1]Patent: WO2011/73263,2011,A1
[2]Patent: WO2018/167147,2018,A1
[3]Patent: WO2020/12424,2020,A1

4
[ 1072-97-5 ]
[ 1111638-02-8 ]

Reference： [1]Patent: WO2011/73263,2011,A1
[2]Patent: WO2020/12424,2020,A1

5
[ 67-56-1 ]
[ 1111638-02-8 ]
[ 76-02-8 ]
[ 1228551-75-4 ]

Yield	Reaction Conditions	Operation in experiment
88%		Step 4 : 5-Bromo-2-methyl-lH-pyrr -blpyridine-3-carboxylic acid methyl esterAluminium trichloride (179 g, 1.34 mol) was added to a mixture of 5-bromo-2-methyl- lH-pyrrolo[2,3-b]pyridine (81 g, 384 mmol) in dichloromethane (1.5 L) and stirred for 50 minutes. Trichloroacetyl chloride (238 g, 147 mL, 1.31 mol) was added and the reaction mixture was left to stir for 18 hours. The reaction mixture was cooled to 0 C and quenched by the addition of methanol (500 mL). The solvent was evaporated and the resultant residue treated with a mixture of potassium hydroxide (320 g) in methanol (2 L) (caution - exotherm) and the reaction mixture then heated under reflux for 3 hours. The reaction mixture was allowed to cool to ambient temperature then evaporated. The resultant residue was treated with 2M hydrochloric acid to give an acidic mixture. The resulting mixture was extracted with ethyl acetate (x 5), the combined organic layer dried (Na2S04), filtered and evaporated then triturated with diethyl ether to afford the title compound as a buff solid (91 g, 88%). NMR (300 MHz, DMSO-d6): 12.63 (s, 1H), 8.31 (s, 2H), 3.83 (s, 3H), 2.68 (s, 3H).

Reference： [1]Patent: WO2011/73263,2011,A1 .Location in patent: Page/Page column 79-80

6
[ 1111638-02-8 ]
[ 1200130-70-6 ]