[ CAS No. 1075-26-9 ] {[proInfo.proName]}

Name: 1075-26-9|(1H-Indol-6-yl)methanol|98%
Brand: Ambeed
SKU: A562554
Price: 14.0 USD
Availability: InStock
Rating: 96 (30 reviews)

,{[proInfo.pro_purity]}

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

DV 2D 3D

3d Animation Molecule Structure of 1075-26-9

Structure of 1075-26-9 * 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 [ 1075-26-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1075-26-9 ]

SDS Specification

Alternatived Products of [ 1075-26-9 ]

Product Details of [ 1075-26-9 ]

CAS No. :	1075-26-9	MDL No. :	MFCD02179595
Formula :	C₉H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WRMZOPANDOHWJU-UHFFFAOYSA-N
M.W :	147.17	Pubchem ID :	2773459
Synonyms :

Safety of [ 1075-26-9 ]

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 [ 1075-26-9 ]

* 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.

Upstream synthesis route of [ 1075-26-9 ]
Downstream synthetic route of [ 1075-26-9 ]

[ 1075-26-9 ] Synthesis Path-Upstream 1~5

1
[ 1075-26-9 ]
[ 21005-45-8 ]

Yield	Reaction Conditions	Operation in experiment
24%	Stage #1: With Dess-Martin periodane In dichloromethane for 1 h; Stage #2: With sodium hydroxide In dichloromethane; water for 0.5 h;	a) 1 -Methyl- lH-indole-6-carbaldehyde; Dess-Martin periodane (2.56 g, 6.04 mmol) was dissolved into anhydrous CH₂Cl₂ (25 ml). (lH-Indol-6-yl)-methanol (883 mg, 6.04 mmol) in anhydrous CH₂Cl₂ (20 ml) was added and the mixture was stirred for 1 h. Aqueous sodium hydroxide (12 ml of IN solution) was added and the reaction was stirred for 30 min. The organic layer was separated and washed with water (10 ml), brine (10 ml), dried over MgSO₄, filtered and concentrated to a thick brown oil. Purification by column chromatography (silica gel, gradient elution of 2percent MeOH/CH₂Cl₂ to 5percent MeOH/CH₂Cl₂) gave lH-indole-6-carbaldehyde (212 mg, 24percent) as a brown solid: ¹H NMR (300 MHz, DMSO-d₆) δ 11.67 (bs, IH), 9.99 (s, IH), 7.97 (s, IH), 7.70-7.65 (m, 2H), 7.54-7.50 (m, IH), 6.59-5.54 (m, IH).

Reference： [1] Patent: WO2007/53131, 2007, A2, . Location in patent: Page/Page column 157

2
[ 1075-26-9 ]
[ 1196-70-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With manganese dioxide In dichloromethane	b. 6-Formylindole Manganese dioxide (240 g) was added to a mechanically stirred solution of 6-hydroxymethylindole (40.7 g) in methylene chloride (1.6 liter). The mixture was stirred for 18 hr, filtered through a pad of diatomaceous earth, the filter cake washed with methylene chloride and chloroform, and the filtrate evaporated to give 6-formylindole (30.55 g) as a yellow solid. The filter cake was washed with tetrahydrofuran and the washings evaporated to give a further crop of 6-formylindole (2.35 g, 82percent combined yield); partial NMR (250 MHz, DMSO-d₆): 6.58(m, 1H, H³ -indole), 10.00(s, 1H, CHO), 11.71(br s, 1H, NH).
56%	Stage #1: With Dess-Martin periodane In dichloromethane for 1 h; Stage #2: With sodium hydroxide In dichloromethane; water for 0.25 h;	Dess-Martin periodinane (1.53 g, 2.6 mmol) was dissolved into methylene chloride (15 mL). Indol-6-yl-methanol (500 mg, 3.4 mmol) in methylene chloride (12 mL) was added and the mixture was stirred for 1 hr. Sodium hydroxide (5 mL of 1 N solution) was added and the reaction was stirred for 15 min. The organic layer was separated and washed with H20 (5 mL), brine (5 mL), dried over MGS04 and concentrated to afford the title compound as a brown solid (275 mg, 56percent). TH NMR (300 MHz, DMSO-D6) 8 11.7 (s, 1H), 9.98 (s, 1H), 7.97 (s, 1H), 7.70-7. 65 (m, 2H), 7.52 (dd, J= 8.2, 1.4 Hz, 1H), 6.57-6. 5 (m, 1H).

Reference： [1] Patent: US4894386, 1990, A,
[2] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4109 - 4115
[3] Patent: WO2004/52890, 2004, A1, . Location in patent: Page 46-47; 93-94
[4] Patent: US5281593, 1994, A,
[5] Patent: EP469833, 1992, A1,

3
[ 32989-68-7 ]
[ 1196-70-9 ]
[ 1075-26-9 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4109 - 4115

4
[ 32989-68-7 ]
[ 1196-70-9 ]
[ 1075-26-9 ]
[ 111596-29-3 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4109 - 4115
[2] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4109 - 4115

5
[ 31680-07-6 ]
[ 1196-70-9 ]
[ 1075-26-9 ]
[ 111596-29-3 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 10, p. 4109 - 4115

[ 1075-26-9 ] Synthesis Path-Downstream 1~38

1
[ 1075-26-9 ]
[ 1196-70-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With manganese dioxide; In dichloromethane;	b. 6-Formylindole Manganese dioxide (240 g) was added to a mechanically stirred solution of 6-hydroxymethylindole (40.7 g) in methylene chloride (1.6 liter). The mixture was stirred for 18 hr, filtered through a pad of diatomaceous earth, the filter cake washed with methylene chloride and chloroform, and the filtrate evaporated to give 6-formylindole (30.55 g) as a yellow solid. The filter cake was washed with tetrahydrofuran and the washings evaporated to give a further crop of 6-formylindole (2.35 g, 82% combined yield); partial NMR (250 MHz, DMSO-d6): 6.58(m, 1H, H3 -indole), 10.00(s, 1H, CHO), 11.71(br s, 1H, NH).
56%		Dess-Martin periodinane (1.53 g, 2.6 mmol) was dissolved into methylene chloride (15 mL). Indol-6-yl-methanol (500 mg, 3.4 mmol) in methylene chloride (12 mL) was added and the mixture was stirred for 1 hr. Sodium hydroxide (5 mL of 1 N solution) was added and the reaction was stirred for 15 min. The organic layer was separated and washed with H20 (5 mL), brine (5 mL), dried over MGS04 and concentrated to afford the title compound as a brown solid (275 mg, 56%). TH NMR (300 MHz, DMSO-D6) 8 11.7 (s, 1H), 9.98 (s, 1H), 7.97 (s, 1H), 7.70-7. 65 (m, 2H), 7.52 (dd, J= 8.2, 1.4 Hz, 1H), 6.57-6. 5 (m, 1H).
	In hexane; dichloromethane;	ii) 6-Formyl indole To a solution of 6-hydroxymethyl indole (4.9 g, 33.3 mmol) in dry dichloromethane (200 ml) was added a solution of pyridinium dichromate (15.97 g, 42.5 mmol) in dry dichloromethane (100 ml) and the suspension stirred at room temperature for 5 hours. The suspension was diluted with diethyl ether and filtered through a pad of silica to give an orange solution, which was evaporated in vacuo. The crude solid was purified by flash chromatography on silica, eluding with 50% diethyl ether in hexane, to yield a pale orange solid. Recrystallisation from diethyl ether/40-60 C. petrol gave a pale orange crystalline solid, m.p. 126-128 C.

In hexane; dichloromethane;

ii) 6-Formyl indole To a solution of 6-hydroxymethyl indole (4.9 g, 33.3 mmol) in dry dichloromethane (200 ml) was added a solution of pyridinium dichromate (15.97 g, 42.5 mmol) in dry dichloromethane (100 ml) and the suspension stirred at room temperature for 5 hours. The suspension was diluted with diethyl ether and filtered through a pad of silica to give an orange solution, which was evaporated in vacuo . The crude solid was purified by flash chromatography on silica, eluding with 50% diethyl ether in hexane, to yield a pale orange solid. Recrystallisation from diethyl ether/40 - 60 C. petrol gave a pale orange crystalline solid, m.p. 126 - 128 C.

Reference： [1]Patent: US4894386,1990,A
[2]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4109 - 4115
[3]Patent: WO2004/52890,2004,A1 .Location in patent: Page 46-47; 93-94
[4]Patent: US5281593,1994,A
[5]Patent: EP469833,1992,A1
[6]ACS Infectious Diseases,2020,vol. 6,p. 572 - 576

2
[ 31680-07-6 ]
[ 1196-70-9 ]
[ 1075-26-9 ]
[ 111596-29-3 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4109 - 4115

3
[ 32989-68-7 ]
[ 1196-70-9 ]
[ 1075-26-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4109 - 4115

Yield	Reaction Conditions	Operation in experiment
	With diisobutylaluminium hydride; In dichloromethane; at -78℃; for 2h;	General procedure: TThhee ttiittllee c coommppoouunndd wwaass pprreeppaarreedd bbyy rreedduuccttiioonn ooff mmeetthhyyll 11--((((33--((ttrrilfflluuoorroommeetthhyyl})pphheennyyll))ssuullffoonnyyll 11 HH--iinnddoollee--55--ccaarrbbooxxyllaattee ((8800 mmgg,, 00..2211 mmmmooli)) wwiitthh DDIIBBAALL--HH 1 iivvll iinn DDCCMM ((441177 ppLL,, 00..4422 mmmmooii)) aaccccoorrddiinngg ttoo GGeenneerraall PPrroocceedduurree BB.. TThhee eexxttraraccttiioonn p prroovviiddeedd 7744 mmgg ( (9999%%)) ooff aa tthhee ttiittllee ccoommppoouunndd aass aa ccoolloorrlleessss ooiill wwhhiicchh wwaass uusseedd wwiitthhoouutt ffuurtrthheerr ppuuririffiiccaattiioonn;; 11HH NNMMRR ((440000MMHHzz,, MeeOODD)) deltadelta ~~ 88..1166 ( (ss,, 11 HH)),, 88..1133 ( (dd,, JJ == 88..11 HHzz,, 11 HH)),, 77..9977 ( (dd,, J J''~~ 88..66 HHzz,, 11 HH)),, 77..8844 ((dd,, JJ ~~ 88..33 HHzz,, 11 HH)),, 77..6668 ((dd,, JJ == 33..77 HHzz,, 11 H H)),, 77..6666 -- 77..6611 ((mm,, 11 H H)),, 77,.5511 ( (dddd,, JJ " 00..77,, 11 ..55 HHzz,, 11 HH)),, 77..3355 ( (dddd,, -J J ~ = ..33,, 88..66 HHzz,, 11 HH)),, 66..7733 ((dddd,, JJ == 00..99,, 33..77 HHzz,, 11 H H)),, 44..6633 ((ss,, 22 H H)).. General Procedure B* Reduction of methyl indole ester. To the solution of methyl N-sulfonyl indole ester f 1eq,) in anhydrous DCM (C: 0.2 mmol/mL) at -?8C was added dropwise a soiuiion of PIBAL-H at 1M in. DCM (2 eq.). The reaction was stirred at -78CC for 2h. The completion of the reaction was monitored by HPLC. Upon completion, H2O was added and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCOa, brine and dried over NaaS.CH. Filtration and removal of the solvent provided the desired product, which was used without further purification.

6
[ 50820-65-0 ]
[ 1075-26-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 3h;Under nitrogen;	Preparation XLVII 6-((triisopropylsilyloxy)methyl)indole indole-6-carboxylic Acid Methyl Ester [0339] To a solution of indole-6-carboxylic acid (39.5 g, 245 mmol) in methanol (200 mL) and dichloromethane (750 mL) was added 2 M (trimethylsilyl)diazomethane in hexanes (160 mL, 320 mmol) dropwise over 1 hour. The reaction was stirred at room temperature overnight. The following day the reaction was concentrated to a thick brown crude oil that was diluted with ethyl acetate (500 mL) and washed with saturated aqueous sodium bicarbonate (2×200 mL), saturated aqueous sodium chloride (2×200 mL) and dried over sodium sulfate. The mixture was then filtered and the filtrate concentrated under reduced pressure to form a suspension. The suspension was filtered to provide 43 g of the desired compound as an off-white solid. [0340] 6-(hydroxymethyl)indole [0341] To a solution of indole-6-carboxylic acid methyl ester (20.0 g, 114 mmol) in anhydrous tetrahydrofuran (1.6 L) stirring under nitrogen at room temperature was added carefully lithium aluminum hydride (8.7 g, 230 mmol) while purging with nitrogen. Following this addition, the reaction mixture was stirred at room temperature for 3 hours and was then cooled to 0 C. This mixture was treated sequentially with water (9 mL), 15% sodium hydroxide (9 mL), and additional water (25 mL). The resulting suspension was filtered and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 30%-60% ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 16.0 g (95%) of the desired compound as an off-white solid. [0342] IS-MS, m/e 146.0 (m-1). [0343] Silylation [0344] To a solution of 6-(hydroxymethyl)indole (16.0 g, 110 mmol) in dichloromethane (800 mL) stirring at 0 C. under nitrogen was added triethylamine (22.5 mL, 160 mmol). Next a prepared solution of triisopropylsilyl trifluoromethanesulfonate (30.5 mL, 115 mmol) in dichloromethane (200 mL) was added slowly using an addition funnel. The reaction was stirred at 0 C. for 3 hours. The reaction was then diluted with dichlormethane (200 mL) and washed with water (2×200 mL), saturated aqueous sodium chloride (2×200 mL) and dried over sodium sulfate. The solution was filtered and the filtrate concentrated under reduced pressure. The residue was sujected to silica gel chromatography. Fractions containing product were combined and concentrated under reduced pressure to provide the title compound. [0345] IS-MS, m/e 302 (m-1).
	With hydrogenchloride; In tetrahydrofuran; sodium-dried tetrahydrofuran; water;	EXAMPLE 9 6-Hydroxymethyl indole Lithium aluminium hydride (3.48 g, 91.70 mmol) was suspended in sodium-dried tetrahydrofuran (150 ml). The suspension was stirred under a nitrogen atmosphere. Methyl-(indol-6-yl)methanoate (8.0 g, 45.7 mmol) was dissolved in dry tetrahydrofuran (50 ml) and added dropwise to the lithium aluminium hydride suspension. The mixture was stirred at ambient temperature for three hours. Water (10 ml) was added dropwise, followed by 2N hydrogen chloride (30 ml). The mixture was extracted with diethyl ether (3*150 ml) to yield a light purple oil.
2.05 g		To a suspension of lithium aluminium hydride (0.866 g; 22.82 mmol) in dry THF (30 mL) cooled at 0 C was added a solution of methyl 1 /-/-indole-6-carboxylate (2.000 g; 1 1 .42 mmol) in THF (30 mL) under nitrogen atmosphere. The reaction mixture was stirred at room temperature overnight. The reaction was quenched by careful addition of a 1 N Rochelle salt solution. The reaction mixture was stirred at room temperature for 2 h and was then extracted with dichloromethane. The phases were separated. The organic phase was dried over magnesium sulfate and evaporated under reduced pressure to afford 2.050 g of (1 /-/-indolyl-6-yl)methanol as a yellow oil which was used in the next step without further purification. ESI/APCI(-): 146 (M- H).

Reference： [1]Patent: US2003/229026,2003,A1 .Location in patent: Page 24
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3217 - 3220
[3]Patent: US5563147,1996,A
[4]Patent: WO2013/45516,2013,A1 .Location in patent: Page/Page column 186; 187
[5]ACS Infectious Diseases,2020,vol. 6,p. 572 - 576

7
[ 1075-26-9 ]
[ 80522-42-5 ]
[ 345264-55-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3217 - 3220

8
[ 1075-26-9 ]
[ 345264-56-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3217 - 3220

9
[ 1075-26-9 ]
oxo-(6-triisopropylsilanyloxymethyl-1H-indol-3-yl)-acetyl chloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3217 - 3220

10
[ 1075-26-9 ]
[ 345261-66-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3217 - 3220

11
[ 1075-26-9 ]
N-[(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-oxo-acetyl]-2-(6-triisopropylsilanyloxymethyl-1H-indol-3-yl)-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3217 - 3220

12
[ 1075-26-9 ]
[ 40863-49-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4109 - 4115
[2]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4109 - 4115

13
[ 1075-26-9 ]
[ 40863-48-7 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4109 - 4115

14
[ 1075-26-9 ]
[ 85864-10-4 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4109 - 4115

15
[ 31680-07-6 ]
[ 1075-26-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4109 - 4115

16
[ 40870-59-5 ]
[ 1075-26-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4109 - 4115

17
triisopropylsilyl trifluoromethanesulfonate [ No CAS ]
[ 1075-26-9 ]
[ 345264-55-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 3h;Under nitrogen;	Preparation XLVII 6-((triisopropylsilyloxy)methyl)indole indole-6-carboxylic Acid Methyl Ester [0339] To a solution of indole-6-carboxylic acid (39.5 g, 245 mmol) in methanol (200 mL) and dichloromethane (750 mL) was added 2 M (trimethylsilyl)diazomethane in hexanes (160 mL, 320 mmol) dropwise over 1 hour. The reaction was stirred at room temperature overnight. The following day the reaction was concentrated to a thick brown crude oil that was diluted with ethyl acetate (500 mL) and washed with saturated aqueous sodium bicarbonate (2×200 mL), saturated aqueous sodium chloride (2×200 mL) and dried over sodium sulfate. The mixture was then filtered and the filtrate concentrated under reduced pressure to form a suspension. The suspension was filtered to provide 43 g of the desired compound as an off-white solid. [0340] <strong>[1075-26-9]6-(hydroxymethyl)indole</strong> [0341] To a solution of indole-6-carboxylic acid methyl ester (20.0 g, 114 mmol) in anhydrous tetrahydrofuran (1.6 L) stirring under nitrogen at room temperature was added carefully lithium aluminum hydride (8.7 g, 230 mmol) while purging with nitrogen. Following this addition, the reaction mixture was stirred at room temperature for 3 hours and was then cooled to 0 C. This mixture was treated sequentially with water (9 mL), 15% sodium hydroxide (9 mL), and additional water (25 mL). The resulting suspension was filtered and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 30%-60% ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 16.0 g (95%) of the desired compound as an off-white solid. [0342] IS-MS, m/e 146.0 (m-1). [0343] Silylation [0344] To a solution of <strong>[1075-26-9]6-(hydroxymethyl)indole</strong> (16.0 g, 110 mmol) in dichloromethane (800 mL) stirring at 0 C. under nitrogen was added triethylamine (22.5 mL, 160 mmol). Next a prepared solution of triisopropylsilyl trifluoromethanesulfonate (30.5 mL, 115 mmol) in dichloromethane (200 mL) was added slowly using an addition funnel. The reaction was stirred at 0 C. for 3 hours. The reaction was then diluted with dichlormethane (200 mL) and washed with water (2×200 mL), saturated aqueous sodium chloride (2×200 mL) and dried over sodium sulfate. The solution was filtered and the filtrate concentrated under reduced pressure. The residue was sujected to silica gel chromatography. Fractions containing product were combined and concentrated under reduced pressure to provide the title compound. [0345] IS-MS, m/e 302 (m-1).

Reference： [1]Patent: US2003/229026,2003,A1 .Location in patent: Page 24

18
[ 1670-82-2 ]
[ 1075-26-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With lithium aluminium tetrahydride; In tetrahydrofuran;	<strong>[1670-82-2]Indole-6-carboxylic acid</strong> (1.0 g, 6.2 mmol) was dissolved into anhydrous THF (20 mL) under argon. Lithium aluminum hydride (494 mg, 13 mmol) was added portionwise and the mixture was stirred overnight. The mixture was cooled to 0C and ethyl acetate (10 mL) was carefully added, followed by methanol (5 mL) and water (5 mL). The mixture was stirred for 30 min. and filtered through celite. The solution was concentrated and dissolved into ethyl acetate (200 mL) and washed with brine (2 x 20 mL), dried over MGS04 and concentrated to afford the title compound as a brown oil (880 mg, 96%). 1H NMR (300 MHz, CDC13) 8 8.30 (s, 1H), 7.58 (d, J= 8.1 Hz, 1H), 7.23 (d, J= 1.1 Hz, 1H), 7.13-7. 05 (m, 2H), 6.51-6. 49 (m, 1H), 4.70 (s, 2H).

Reference： [1]Patent: WO2004/52890,2004,A1 .Location in patent: Page 46-47; 93

19
NaH(8.2mm) [ No CAS ]
[ 1075-26-9 ]
[ 7732-18-5 ]
[ 74-88-4 ]
[ 202745-68-4 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; N,N-dimethylformamide ("DMF"); acetic anhydride (Ac2 O); N,N-dimethyl-formamide;	a Acetic acid 1-methyl-1H-indol-6-yl methyl ester NaH(8.2mm) in N,N-dimethylformamide ("DMF") (20 mL) was cooled to 0 C., then treated with a solution of the known <strong>[1075-26-9]1H-<strong>[1075-26-9]indole-6-methanol</strong></strong> (1 g,6.8 mm) in DMF(8 mL). After stirring for 1 hour at 0 C., methyl iodide ("MeI") (0.51 mL, 8.2 mm) dissolved in DMF (2 mL) was added, and the mixture was stirred at 0 C. overnight, then poured into ice/H2 O (250 ml) and extracted with EtOAc(50 mL*3). The organic fraction was dried over MgSO4, filtered, evaporated and purified by flash column chromatography to afford 1-methyl-<strong>[1075-26-9]1H-<strong>[1075-26-9]indole-6-methanol</strong></strong> (0.82 g. 75%). This product (1-methyl-<strong>[1075-26-9]1H-<strong>[1075-26-9]indole-6-methanol</strong></strong>, 1 g, 6.2 mm) was dissolved in a mixture of pyridine (5 mL) and acetic anhydride (Ac2 O) (5 mL) and stirred at room temperature overnight. The solvent was evaporated, and the residue purified by flash column chromatography to afford 1.09 g of Acetic acid 1-methyl-1H-indol-6-yl methyl ester.

Reference： [1]Patent: US5856517,1999,A

20
[ 1075-26-9 ]
[ 3420-02-8 ]

Yield	Reaction Conditions	Operation in experiment
	palladium on charcoal; In ethanol; chloroform; acetic acid;	6-Methyl indole 6-hydroxymethyl indole (6.135 g, 41.69 mmol) was dissolved in ethanol (70 ml). 10% Palladium on charcoal (0.610 g) was suspended in acetic acid (70 ml) and added to the ethanol (70 ml) solution. The mixture was placed on the high pressure hydrogenator at 60 psi. After 20 hours, the mixture was filtered through Celite and the resulting solution concentrated in vacuo. The mixture was purified by flash chromatography using chloroform as solvent to yield a colourless oil.

Reference： [1]Patent: US5563147,1996,A

21
aqueous sodium sulfate [ No CAS ]
[ 50820-65-0 ]
[ 1075-26-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With hydrogenchloride; diisobutylaluminium hydride; In methanol; toluene;	a. 6-Hydroxymethylindole A stirred solution of methyl indole-6-carboxylate (50 g) (see Example 1, part b) in dry toluene (1 liter), in a three-necked three-liter flask fitted with a mechanical stirrer, thermometer and dropping funnel, was cooled to -70 under an atmosphere of nitrogen, and treated dropwise with a solution of diisobutylaluminum hydride (381 ml of 1.5M solution in toluene) over 50 min. After 2.5 hr a further portion of diisobutylaluminum hydride (25 ml) was added dropwise, and the mixture stirred for a further 30 min. Methanol (100 ml) and saturated aqueous sodium sulfate (100 ml) were added sequentially, at -78. The cooling bath was removed, the reaction allowed to warm to room temperature, and 6M hydrochloric acid (25 ml) was added dropwise. The mixture was filtered through a pad of diatomaceous earth, the filter cake washed with toluene and water, the organic phase separated and washed with water, dried (MgSO4) and evaporated to give 6-hydroxymethylindole (34.2 g, 82%) as an oil which slowly solidified; partial NMR (250 MHz, CDCl3): 1.73(s, 1H, CH2 OH), 4.78(s, 2H, CH2 OH), 6.55(m, 1H, H3 -indole), 8.20(br s, 1H, NH).

Reference： [1]Patent: US4894386,1990,A

22
[ 1075-26-9 ]
[ 74-88-4 ]
[ 202745-68-4 ]

Yield	Reaction Conditions	Operation in experiment
	With NaH; In pyridine; N,N-dimethylformamide (DMF); water; acetic anhydride; N,N-dimethyl-formamide;	a) Acetic acid 1-methyl-1H-indol-6-yl methyl ester NaH (8.2mM) in N,N-dimethylformamide (DMF) (20ml) was cooled to 0C, then treated with a solution of the known <strong>[1075-26-9]1H-<strong>[1075-26-9]indole-6-methanol</strong></strong> (1g, 6.8mM) in DMF (8ml). After stirring for 1 hour at 0C, methyl iodide (MeI,.51ml, 8.2mM) dissolved in DMF (2ml) was added, and the mixture was stirred at 0C overnight, then poured into ice/H2O (250ml) and extracted with EtOAc (50ml x 3). The organic fraction was dried over MgSO4, filtered, evaporated and purified by flash column chromatography to afford 1-methyl-<strong>[1075-26-9]1H-<strong>[1075-26-9]indole-6-methanol</strong></strong> (.82g. 75%). This product (1-methyl-<strong>[1075-26-9]1H-<strong>[1075-26-9]indole-6-methanol</strong></strong>, 1g, 6.2mM) was dissolved in a mixture of pyridine (5ml) and acetic anhydride (Ac2O, 5ml) and stirred at room temperature overnight. The solvent was evaporated, and the residue purified by flash column chromatography to afford 1.09g of acetic acid 1-methyl-1H-indol-6-yl methyl ester.

Reference： [1]Patent: EP915872,2003,B1

23
[ 1075-26-9 ]
[ 21005-45-8 ]

Yield	Reaction Conditions	Operation in experiment
24%		a) 1 -Methyl- lH-indole-6-carbaldehyde; Dess-Martin periodane (2.56 g, 6.04 mmol) was dissolved into anhydrous CH2Cl2 (25 ml). (lH-Indol-6-yl)-methanol (883 mg, 6.04 mmol) in anhydrous CH2Cl2 (20 ml) was added and the mixture was stirred for 1 h. Aqueous sodium hydroxide (12 ml of IN solution) was added and the reaction was stirred for 30 min. The organic layer was separated and washed with water (10 ml), brine (10 ml), dried over MgSO4, filtered and concentrated to a thick brown oil. Purification by column chromatography (silica gel, gradient elution of 2% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2) gave lH-indole-6-carbaldehyde (212 mg, 24%) as a brown solid: 1H NMR (300 MHz, DMSO-d6) delta 11.67 (bs, IH), 9.99 (s, IH), 7.97 (s, IH), 7.70-7.65 (m, 2H), 7.54-7.50 (m, IH), 6.59-5.54 (m, IH).

Reference： [1]Patent: WO2007/53131,2007,A2 .Location in patent: Page/Page column 157

24
[ 1075-26-9 ]
[ 18162-48-6 ]
[ 1203656-83-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In dichloromethane; at 0 - 20℃;	tert-Butyldimethylsilyl chloride (2.20 g, 14.6 mmol, 1.2 eq) was added to a solution of 6-hydroxymethylindole (1.78 g, 12.1 mmol, 1.0 eq) and triethylamine (5.00 ml, 36.3 mmol, 3.0 eq) in CH2CI2 (20 ml) at 0C. The reaction was allowed to reach room temperature and stirred for 16 h. Water (50 ml) was added and the product was extracted with CH2CI2 (3 x 50 ml). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica using EtOAc and hexane as an eluent to provide (7) off-white solid (2.85 g, 10.9 mmol, 90%).
0.482 g		To a solution of (1 /-/-indol-6-yl)methanol (0.500 g; 3.397 mmol) in dry THF (20 mL) cooled at 0 C was added portionwise sodium hydride (60% in mineral oil; 0.271 g; 6.775 mmol). After stirring for 5 min, TBDMSCI (0.512 g; 3.397 mmol) was added. The resulting solution was stirred at room temperature for 1 h. The reaction mixture was diluted with dichloromethane and washed with a saturated sodium bicarbonate solution. The phases were separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (2% to 20%) in heptane furnished 0.482 g (46% over 2 steps) of Q-{{{tert- butyldimethylsilyl)oxy)methyl)-1 H-indole as a white solid. ESI/APCI(+): 262 (M+H). ESI/APCI(-): 260 (M-H).

Reference： [1]Patent: WO2010/1179,2010,A2 .Location in patent: Page/Page column 57-58
[2]Patent: WO2013/45516,2013,A1 .Location in patent: Page/Page column 187

25
[ 1075-26-9 ]
[ 1359945-97-3 ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 373 - 377

26
[ 1075-26-9 ]
indolin-6-ylmethanol [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 373 - 377

27
[ 1075-26-9 ]
[ 1428972-84-2 ]

Reference： [1]Patent: WO2013/45516,2013,A1

28
[ 1075-26-9 ]
[ 1428969-33-8 ]

Reference： [1]Patent: WO2013/45516,2013,A1

29
[ 1196-70-9 ]
[ 1075-26-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With [Ir(2,2':6',2'?-terpyridine)(1,10-phenanthroline)Cl](PF6)2; sodium formate; In ethanol; water; at 100℃; for 0.75h;Microwave irradiation;	General procedure: An aldehyde (1 mmol),sodium formate (4.5 eq), and catalyst (0.2 mol%) were taken in70% ethanol in water (4 mL) in a microwave vial and vortexed togenerate a homogenous solution. The mixture was heated in MWat 100 C using 150W of irradiation. Reaction progress was monitored by TLC. If complete conversion took place, the reaction colorturns to emerald green (color disappears after sometime) from paleyellow, and byproduct Na2CO3 precipitates. The Na2CO3 solid wasremoved by decanting the supernatant. The solid was washed withethyl acetate (20 mL). The combined decanted solution waswashed with water (5.0 mL), followed by brine solution (5.0 mL),dried over Na2SO4, filtered, and evaporated to dryness to affordthe desired alcohol as a pale-yellow liquid or off-white solid.
34%	With hydrogenchloride; borane pyridine; In ethanol; water; at 0 - 20℃; for 21h;Inert atmosphere;	Under a nitrogen atmosphere, to a flask, 1.0 g (6.89 mmol) of the compound (x1), 20 mL of ethanol, and 3.84 g (41.33 mmol) of pyridineborane were added, 11 mL of a 6M aqueous hydrochloric acid solution was dropped under ice cooling, and it was stirred at 0 C. for three hours, and at room temperature for 18 hours. After that, 50 mL of a saturated aqueous sodium hydrogen carbonate solution was added under ice cooling, and extraction was performed with 100 mL of ethyl acetate. An obtained organic layer was dried with anhydrous sodium sulfate, a solvent was removed by using an evaporator, and then refinement was performed by column chromatography using hexane/ethyl acetate (3:2, volume ratio) as a developing solution, to thereby obtain a compound (x2) (0.35 g, 2.24 mmol). A yield from the compound (x1) was 34%.

Reference： [1]Journal of Catalysis,2019,vol. 378,p. 283 - 288
[2]Patent: US2018/346729,2018,A1 .Location in patent: Paragraph 0314-0316

30
[ 75-30-9 ]
[ 1075-26-9 ]
[ 202745-77-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tetra-(n-butyl)ammonium iodide; potassium hydroxide; In tetrahydrofuran; water; at 80℃; for 15h;	To a flask, 0.35 g (2.24 mmol) of the compound (x2), 85 mg (0.23 mmol) of tetrabutylammonium iodide, 10 mL of a 33 weight % aqueous potassium hydroxide solution, and 10 mL of tetrahydrofuran were added, 1.99 g of 2-iodopropane was dropped, and it was stirred at 80 C. for 15 hours. After that, 100 mL of water was added, a major part of tetrahydrofuran was removed by using an evaporator, and then extraction was performed with 100 mL of ethyl acetate. An obtained organic layer was dried with anhydrous sodium sulfate, a solvent was removed by using an evaporator, and then refinement was performed by column chromatography using hexane/ethyl acetate (1:1, volume ratio) as a developing solution, to thereby obtain a compound (x3) (0.39 g, 1.95 mmol). A yield from the compound (x2) was 87%.

Reference： [1]Patent: US2018/346729,2018,A1 .Location in patent: Paragraph 0314; 0317; 0318

31
[ 1075-26-9 ]
C₂₈H₃₂N₂O₄ [ No CAS ]