Methanol → 3-(2,4-Dichlorophenyl)-6-(2-ethyl-5-hydroxymethyl-2H-pyrazol-3-yl) 1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one

HRID 559161Notes

Reaction equation

HRID 559161 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15]2[N:21]([CH3:34])[C:22](=[O:33])[C:23]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=4[Cl:32])=[CH:24][C:14]3=2)[N:8]([CH2:35][CH3:36])[N:7]=1)=O)C.[BH4-].[Na+].C(Cl)Cl.CO>C(O)C>[Cl:32][C:26]1[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=1[C:23]1[C:22](=[O:33])[N:21]([CH3:34])[C:15]2[N:16]([CH3:20])[C:17]3[C:13]([C:14]=2[CH:24]=1)=[CH:12][C:11]([C:9]1[N:8]([CH2:35][CH3:36])[N:7]=[C:6]([CH2:4][OH:3])[CH:10]=1)=[CH:19][CH:18]=3

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 669980725-[3-(2,4-Dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-1-ethyl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 669985353-(2,4-Dichlorophenyl)-6-(2-ethyl-5-hydroxymethyl-2H-pyrazol-3-yl) 1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

450 mg (0.86 mmol) of compound from Example 59, 5-[3-(2,4-dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-1-ethyl-1H-pyrazole-3-carboxylic acid ethyl ester, are dissolved in 10 ml of absolute ethanol and 42 mg (1.12 mmol) of NaBH4 are added. The mixture is refluxed overnight. The reaction medium is allowed to return to ambient temperature, CH2Cl2 and MeOH are added, and the product is adsorbed onto silica. Purification is carried out on a silica column, elution being carried our with EtOAc, and then with a 95/05 EtOAc/MeOH mixture. The oil obtained is triturated in ether.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. customto return to ambient temperature
  3. customPurification
  4. washis carried out on a silica column, elution being
  5. customThe oil obtained
  6. customis triturated in ether

Sources & evidence

ORD record
ord-e52744583549405594a5518c4cf643b1
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

Loading…