1-(Cyclohexylmethyl)-N-(3,5-dichloro-1-oxidopyridin-4-yl)-3-methylindole-6-carboxamide

Base Information

• Chemical Name: 1-(Cyclohexylmethyl)-N-(3,5-dichloro-1-oxidopyridin-4-yl)-3-methylindole-6-carboxamide
• CAS No.: 201285-35-0
• Molecular Formula: C22H23Cl2N3O2
• Mol file: 201285-35-0.mol

Synonyms:

Chemical Property of 1-(Cyclohexylmethyl)-N-(3,5-dichloro-1-oxidopyridin-4-yl)-3-methylindole-6-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(Cyclohexylmethyl)-N-(3,5-dichloro-1-oxidopyridin-4-yl)-3-methylindole-6-carboxamide

There total 4 articles about 1-(Cyclohexylmethyl)-N-(3,5-dichloro-1-oxidopyridin-4-yl)-3-methylindole-6-carboxamide 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:

methyl 3-methylindole-6-carboxylate (184151-49-3) → 1-Cyclohexylmethyl-3-methyl-1H-indole-6-carboxylic acid (3,5-dichloro-1-oxy-pyridin-4-yl)-amide (201285-35-0)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / dimethylformamide / 2 h / 0 °C

2: 90 percent / aq. LiOH / methanol / 1 h / 70 °C

3: 1.) 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, (i-Pr)2NEt, 2.) NaAlH₂Et₂ / 1.) CH₂Cl₂, 2.) toluene, 50 deg C, 1 h

With lithium hydroxide; sodium hydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; sodium aluminum diethyl dihydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(98)00572-1

Reference yield:

methyl 3-formyl-6-indolecarboxylate (133831-28-4) → 1-Cyclohexylmethyl-3-methyl-1H-indole-6-carboxylic acid (3,5-dichloro-1-oxy-pyridin-4-yl)-amide (201285-35-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) p-TsOH, p-TsNHNH₂, sulfolane, 2.) NaCNBH₃ / 1.) DMF, 100 deg C, 2.) 100 deg C, 2h

2: NaH / dimethylformamide / 2 h / 0 °C

3: 90 percent / aq. LiOH / methanol / 1 h / 70 °C

4: 1.) 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, (i-Pr)2NEt, 2.) NaAlH₂Et₂ / 1.) CH₂Cl₂, 2.) toluene, 50 deg C, 1 h

With sulfolane; lithium hydroxide; sodium hydride; sodium cyanoborohydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; toluene-4-sulfonic acid hydrazide; sodium aluminum diethyl dihydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(98)00572-1

Reference yield:

methyl 1-cyclohexylmethyl-3-methyl-1 H-indole-6-carboxylate (201286-78-4) → 1-Cyclohexylmethyl-3-methyl-1H-indole-6-carboxylic acid (3,5-dichloro-1-oxy-pyridin-4-yl)-amide (201285-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / aq. LiOH / methanol / 1 h / 70 °C

2: 1.) 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, (i-Pr)2NEt, 2.) NaAlH₂Et₂ / 1.) CH₂Cl₂, 2.) toluene, 50 deg C, 1 h

With lithium hydroxide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; sodium aluminum diethyl dihydride; In methanol;

DOI:10.1016/S0960-894X(98)00572-1

upstream raw materials:

4-amino-3,5-dichloropyridine-N-oxide

1-Cyclohexylmethyl-3-methyl-1 H-indole-6-carboxylic acid

methyl 3-methylindole-6-carboxylate

methyl 3-formyl-6-indolecarboxylate