[ CAS No. 4770-37-0 ] {[proInfo.proName]}

Name: 4770-37-0|Indolin-6-ol|95%
Brand: Ambeed
SKU: A159886
Price: 61.0 USD
Availability: InStock
Rating: 97 (35 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 4770-37-0

Structure of 4770-37-0 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 4770-37-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4770-37-0 ]

SDS Specification

Alternatived Products of [ 4770-37-0 ]

Product Details of [ 4770-37-0 ]

CAS No. :	4770-37-0	MDL No. :	MFCD11559070
Formula :	C₈H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JWLQULBRUJIEHY-UHFFFAOYSA-N
M.W :	135.16	Pubchem ID :	524507
Synonyms :

Calculated chemistry of [ 4770-37-0 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	43.56
TPSA :	32.26 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.29
Log Po/w (XLOGP3) :	1.74
Log Po/w (WLOGP) :	0.79
Log Po/w (MLOGP) :	1.09
Log Po/w (SILICOS-IT) :	1.74
Consensus Log Po/w :	1.33

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.22
Solubility :	0.818 mg/ml ; 0.00605 mol/l
Class :	Soluble
Log S (Ali) :	-2.03
Solubility :	1.25 mg/ml ; 0.00924 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.39
Solubility :	0.547 mg/ml ; 0.00405 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.28

Safety of [ 4770-37-0 ]

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

Application In Synthesis of [ 4770-37-0 ]

* 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 [ 4770-37-0 ]
Downstream synthetic route of [ 4770-37-0 ]

[ 4770-37-0 ] Synthesis Path-Upstream 1~6

1
[ 2380-86-1 ]
[ 4770-37-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium cyanoborohydride In acetic acid at 0 - 20℃; for 3 h; Inert atmosphere	NaBH(CN)₃ (1.4 g, 22.60 mmol) was added slowly to a solution of 8 (1.0 g, 7.51 mmol) in AcOH (20 mL) at 0, and then the mixture was stirred for 3 h at room temperature under N₂ atmosphere. The resulting reaction mixture was quenched with saturated NH₄Cl solution (3 mL) and concentrated under reduced pressure to give the residue, which was redissolved in EtOAc (50 mL), and washed with saturated NaHCO₃ (50 mL), brine (50 mL), dried over anhydrous Na₂SO₄, filtered and concentrated. The residue was purified by flash column chromatography eluting with petroleum ether/ethyl acetate (5:1-3:1-2:1, v/v) to provide the intermediate 9 (0.61 g, 60percent yield) as a brown solid. ¹H NMR (400 MHz, DMSO-d₆) δ 8.73 (s, 1H), 6.75 (d, J = 7.8 Hz, 1H), 6.02–5.86 (m, 2H), 5.31 (s, 1H), 3.35 (t, J = 8.4 Hz, 2H), 2.75 (t, J = 8.3 Hz, 2H). ¹³C NMR (101 MHz, DMSO-d₆) δ 157.01 (s), 153.75 (s), 124.18 (s), 119.01 (s), 103.61 (s), 96.64 (s), 47.06 (s), 28.55 (s).

Reference： [1] ChemMedChem, 2016, vol. 11, # 23, p. 2607 - 2620
[2] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 380 - 396

2
[ 7556-47-0 ]
[ 4770-37-0 ]

Yield	Reaction Conditions	Operation in experiment
22%	at 350℃; for 0.333333 h;	2,3-dihydro-1H-indol-6-ole 0.25 g (1.7 mmol) 6-methoxy-2,3-dihydro-1H-indole and 2.0 g (16.8 mmol) pyridine-hydrochloride were combined and heated to 350° C. for approx. 20 min. Then the reaction mixture was dissolved in acetonitrile/DMF and purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried. Yield: 50 mg (22percent of theoretical) R_t (HPLC-MS): 0.94 min (method O)

Reference： [1] Patent: US2011/21500, 2011, A1, . Location in patent: Page/Page column 49

3
[ 15918-79-3 ]
[ 14572-93-1 ]
[ 7556-21-0 ]
[ 4770-37-0 ]

Reference： [1] Patent: US5256799, 1993, A,

4
[ 496-15-1 ]
[ 4770-37-0 ]
[ 85926-99-4 ]

Reference： [1] Tetrahedron Letters, 1986, vol. 27, # 38, p. 4565 - 4568

5
[ 2042-14-0 ]
[ 4770-37-0 ]

Reference： [1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 380 - 396

6
[ 24239-67-6 ]
[ 4770-37-0 ]

Reference： [1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 380 - 396

[ 4770-37-0 ] Synthesis Path-Downstream 1~48

1
[ 496-15-1 ]
[ 4770-37-0 ]
[ 85926-99-4 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 4565 - 4568

Yield	Reaction Conditions	Operation in experiment
33%		General procedure: Procedure E: Reduction of indoles to indolines. Method I: NaBH3CN (4.23 mmol) was added portion wise over 10 min at 0 C to a solution of alpha,beta-unsaturated system or to an indole (1.06 mmol) in AcOH (7.1 mL) and the mixture was stirred at room temperature from 1 h to overnight. Water (3 mL) was added and the solvent was removed under reduce pressure. The residue was dissolved in EtOAc and washed with saturated NaHCC>3 and brine, dried over MgS04 and evaporated to give the indoline. The indoline hydrochloride was obtained after dissolving an indoline in EtOAc followed by extraction with 2N HC1. The aqueous phase was evaporated to give the reduced salt. An alternative method for the preparation of the indoline hydrochloride involved addition of HC1 gas to a solution of indoline in dry ether.3-(2-(Methoxycarbonyl)ethyl) indolin-5-yl ethylmethylcarbamate, AN-669. Compound AN-669 prepared from AN-785 or AN- 789 by procedure E, was stirred at room temperature over night, was isolated as a white crystals in 23% yield, mp 108-113 C. *H- NMR (300 MHz, D20) ppm delta 7.52 (d, J = 8.4 Hz, 1H, H-4), 7.17-7.25 (m, 2H, H-7+H-6), 4.01-4.16 (m, 1H, H-2'), 3.66 (s, 3H, H-17), 3.55-3.67 (m, 2H, H-2+H-3), 3.31-3.52 (m, 2H, H- l l), 3.08+2.95 (s, 3H, H-13), 2.48-2.52 (m, 2H, H-15), 2.14 (ddd, J = 21.5, 14.7, 7.8 Hz, 1H, H-14), 1.91 (ddd, J = 21.5, 14.7, 7.8 Hz, 1H, H-14), 1.09-1.24 (m, 3H, H-12); 13C- NMR (75 MHz, D20) ppm delta 176.03, 152.30, 145.98, 140.24, 126.94, 122.68, 119.33, 115.81 , 51.57, 51.28, 44.24, 40.52, 33.64, 33.91, 30.94, 27.54, 11.54, 12.19.
	With sodium cyanoborohydride; acetic acid; at 20℃;	General procedure: The title compound was prepared according to General Procedure G from methyl indoe~6- carboxylate (200 mg, 1.14 mmo). The crude product was purified b Combifiash silica gel chromatography (0-30% of EtOAc in hexane), which provided 153 mg (76%) of the title compound as a colorless solid; NMR (400 MHz, CD ) delta - 7.51 (dd, J = 1,5, 7.6 Hz, 1 H), 7.39 (d, J ~ 15 Hz, 1 H), 7.19 (d, J = 7.6 Hz, 1 H), 3.89 (s, 3 H), 3.67 ( , J = 8,5 Hz, 2 H), 3.12 (t, J *= 8,5 Hz, 2 H). General Procedure 6; Reduction of indole in indolin-e. To the solution of indole (1 eq.) in AcOH (C; 0,5 rnmo) at room temperature was added N38H3CN (3 eq.). The reaction was stirred at the same temperature for 2~4h, The completion of the reaction was monitored by HPLC. Upon completion, H2O was added and the reaction mixture was concentrated to dryness. H2O was added to the crude residue and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCCh, brine and dried over a^SQ^ Filtratio and removal of the solvent provided the desired product, which was used without further purification or purified by Combiflash silica gel chromatography to give the corresponding products.

3
[ 15918-79-3 ]
[ 14572-93-1 ]
[ 7556-21-0 ]
[ 4770-37-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; phosphoric acid; hydrogen bromide; In hexane; dichloromethane;	A mixture of 24 g (0.16 mol) of crude 2-(2,4-diaminophenyl)ethanol 4 and 200 ml of 48% hydrobromic acid is heated under reflux for 4 hr and then concentrated in vacuo to leave 109.5 g of a brown semicrystalline mass which is cooled overnight in the refrigerator. The solid is collected and rinsed with ethanol to give 38.66 g (83% if dihydrobromide) of light tan solid. A mixture of 2 g of the hydrobromide and 10 ml of saturated sodium carbonate solution was made strongly alkaline with 1 ml of con. ammonium hydroxide and extracted with 30 ml of ethyl acetate in 3 portions. The organic phases were combined washed with 13 ml of brine and dried over sodium sulfate. Concentration in vacuo left 0.77 g (85%) of brown oil. This oil and 0.56 g of similar material was purified by filtration through 20 ml of silica gel in methylene chloride. The silica was washed with 50 ml of methylene chloride and two 50 ml portions of ethyl acetate. Solid material (1.1 g) was obtained from hexane. That from the first fraction had mp 72-76 and its nmr was consistent with the expected structure. 6-Hydroxyindoline 5 from 6-Aminoindoline 6 - A mixture of 5 g of 6-aminoindoline and 100 g of 30% (w/w) phosphoric acid was stirred and heated in an autoclave at 170-175 for 15 hr. The light brown solution was cooled to room temperature and neutralized with 40 ml of 40% sodium hydroxide solution. It was further diluted to 300 ml with water. The precipitated phosphate salts were filtered off and washed with 200 ml of ethyl acetate in two portions. The organic extracts were separated, combined, washed with 100 ml of brine, dried over sodium sulfate and concentrated in vacuo to leave 4.08 g of red brown oil. This oil was crystallized from hexane to give 3.11 g of crude 6-hydroxyindoline, mp 110-110, as an orange colored solid. Preparation of N-Methyl-6-hydroxyindoline 7.

Reference： [1]Patent: US5256799,1993,A

4
[ 4770-37-0 ]
[ 1158918-65-0 ]
[ 1158918-37-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	Example 53 5-(6-(6-hydroxyindoline-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 150 mg (0.37 mmol) 6-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 50 mg (0.37 mmol) <strong>[4770-37-0]2,3-dihydro-1H-indol-6-ol</strong>, 0.15 mL (0.87 mmol) DIPEA and 130 mg (0.41 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised. Yield: 75 mg (42% of theory) ESI-MS: m/z=491 (M+H)+

Reference： [1]Patent: US2011/21500,2011,A1 .Location in patent: Page/Page column 67

5
[ 7556-47-0 ]
[ 4770-37-0 ]

Yield	Reaction Conditions	Operation in experiment
22%	With pyridine hydrochloride; at 350℃; for 0.333333h;	2,3-dihydro-1H-indol-6-ole 0.25 g (1.7 mmol) 6-methoxy-2,3-dihydro-1H-indole and 2.0 g (16.8 mmol) pyridine-hydrochloride were combined and heated to 350 C. for approx. 20 min. Then the reaction mixture was dissolved in acetonitrile/DMF and purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried. Yield: 50 mg (22% of theoretical) Rt (HPLC-MS): 0.94 min (method O)

Reference： [1]Patent: US2011/21500,2011,A1 .Location in patent: Page/Page column 49

6
[ 4770-37-0 ]
[ 1249768-08-8 ]
1-(2-(5-chlorothiophen-2-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)indolin-6-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sulfuric acid; In butan-1-ol; at 120℃; for 5.0h;	169a) l -C2-C5-Chlorothiophen-2-yn-6.7-dihvdro-5H-cyclopentafdlpyrimidin-4-yl)<strong>[4770-37-0]indolin-6-ol</strong> A solution of 4-chloro-2-(5-chlorothiophen-2-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine ( 10 g, 37.03 mmol, 1 eq), <strong>[4770-37-0]indolin-6-ol</strong> (5 g, 37.03 mmol, 1 eq) and sulfuric acid (6 mL, 1 1 1.0 mmol, 3 eq) in n-butanol ( 1 00 mL) was stirred at 120C for 5 h. The solvent was evaporated under vacuum, ethyl acetate (50 mL) was added, and the precipitate was filtered off. Yield: 10 g (75% of theory)

Reference： [1]Patent: WO2014/170020,2014,A1 .Location in patent: Page/Page column 106

7
[ 4770-37-0 ]
[ 1249768-08-8 ]
2-((1-(2-(5-chlorothiophen-2-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)indolin-6-yl)oxy)-N,N-dimethylethanamine [ No CAS ]

Reference： [1]Patent: WO2014/170020,2014,A1

8
[ 4770-37-0 ]
6-((2-methoxybenzyl)oxy)-1-((3-(trifluoromethyl)phenyl)sulfonyl)indoline [ No CAS ]