(5,6-dimethyl-6H-pyrido[4,3-b]carbazol-11-yl)methanol

Base Information

• Chemical Name: (5,6-dimethyl-6H-pyrido[4,3-b]carbazol-11-yl)methanol
• CAS No.: 89651-48-9
• Molecular Formula: C₁₈H₁₆N₂O
• Molecular Weight: 276.338
• Mol file: 89651-48-9.mol

Synonyms:

Chemical Property of (5,6-dimethyl-6H-pyrido[4,3-b]carbazol-11-yl)methanol

Chemical Property:

• Vapor Pressure: 5.48E-13mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5,6-dimethyl-6H-pyrido[4,3-b]carbazol-11-yl)methanol

There total 11 articles about (5,6-dimethyl-6H-pyrido[4,3-b]carbazol-11-yl)methanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

11-Chloromethyl-11-(2,5-dioxo-pyrrolidin-1-yl)-5,6-dimethyl-6,11-dihydro-5H-pyrido[4,3-b]carbazole-5-carboxylic acid ethyl ester (89651-46-7,89651-47-8) → 11-hydroxymethyl-5,6-dimethyl pyrido<4,3-b>carbazole (89651-48-9)

Guidance literature:

With potassium hydroxide; In water; ethylene glycol; at 160 - 170 ℃;

DOI:10.1016/S0040-4020(01)88606-3

Reference yield:

1-methylindole (603-76-9) → 11-hydroxymethyl-5,6-dimethyl pyrido<4,3-b>carbazole (89651-48-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 63 percent / n-BuLi / tetrahydrofuran / 1 h

2: POCl₃ / pyridine / 1.) room temp, 1 h, 2:) 75 deg C, 1.5 h

3: NaBH₄ / ethanol / 2 h

4: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C

5: 2.) Et₃N / 1.) CH₃Cl, r.t.; 2.) EtOAc, r.t.

6: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature

7: 80 percent / H₂, NaHCO₃ / 10percent Pd-C / ethanol / 5 h / 760 Torr

8: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C

9: 58 percent / CH₂Cl₂ / 1 h / Ambient temperature

10: 77 percent / KOH / H₂O; ethane-1,2-diol / 160 - 170 °C

With potassium hydroxide; sodium tetrahydroborate; n-butyllithium; hydrogen; 10-benzylacridin-10-ium bromide; sodium hydrogencarbonate; triethylamine; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; pyridine; sulfolane; ethanol; dichloromethane; water; ethylene glycol; acetonitrile;

DOI:10.1016/S0040-4020(01)88606-3

Reference yield:

Ethyl α-(N-methylindol-2-yl)acrylate (72938-66-0) → 11-hydroxymethyl-5,6-dimethyl pyrido<4,3-b>carbazole (89651-48-9)

Guidance literature:

Multi-step reaction with 8 steps

1: NaBH₄ / ethanol / 2 h

2: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C

3: 2.) Et₃N / 1.) CH₃Cl, r.t.; 2.) EtOAc, r.t.

4: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature

5: 80 percent / H₂, NaHCO₃ / 10percent Pd-C / ethanol / 5 h / 760 Torr

6: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C

7: 58 percent / CH₂Cl₂ / 1 h / Ambient temperature

8: 77 percent / KOH / H₂O; ethane-1,2-diol / 160 - 170 °C

With potassium hydroxide; sodium tetrahydroborate; n-butyllithium; hydrogen; 10-benzylacridin-10-ium bromide; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; sulfolane; ethanol; dichloromethane; water; ethylene glycol; acetonitrile;

DOI:10.1016/S0040-4020(01)88606-3

upstream raw materials:

11-Chloromethyl-11-(2,5-dioxo-pyrrolidin-1-yl)-5,6-dimethyl-6,11-dihydro-5H-pyrido[4,3-b]carbazole-5-carboxylic acid ethyl ester

6-methylellipticine

1-methylindole

Ethyl α-(N-methylindol-2-yl)acrylate

Downstream raw materials:

11-(bis-2-chloroethyl)amino-5,6-dimethylpyrido<4,3-b>carbazole (HCl-salt)

11-(β-D-ribofuranos-1'-yl)-5,6-dimethylpyrido<4,3-b>-carbazole

11-(2-hydroxyethyl)amino-5,6-dimethyl pyrido<4,3-b>carbazole