Sodium Hydroxide → 3-(4-Bromophenyl)-6-(5-hydroxymethyl-1-methyl-1H-pyrazol-3-yl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one

HRID 559186Notes

Reaction equation

HRID 559186 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:34])[N:8]=[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]([CH3:33])[C:22](=[O:32])[C:23]([C:25]4[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][CH:26]=4)=[CH:24][C:14]3=2)[CH:10]=1)=O)C.[Li+].[BH4-].[OH-].[Na+]>C(Cl)Cl.C1COCC1>[Br:31][C:28]1[CH:29]=[CH:30][C:25]([C:23]2[C:22](=[O:32])[N:21]([CH3:33])[C:15]3[N:16]([CH3:20])[C:17]4[C:13]([C:14]=3[CH:24]=2)=[CH:12][C:11]([C:9]2[CH:10]=[C:6]([CH2:4][OH:3])[N:7]([CH3:34])[N:8]=2)=[CH:19][CH:18]=4)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4148881Lithium borohydride2×HCID 669973785-[3-(4-bromophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 669974103-(4-Bromophenyl)-6-(5-hydroxymethyl-1-methyl-1H-pyrazol-3-yl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-[3-(4-bromophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester are dissolved in 5 ml of anhydrous CH2Cl2 anhydrous. The mixture is refluxed and then 0.2 ml of 1M LiBH4 in THF is added. The mixture is refluxed for 20 hours, while further adding 3 times 0.2 ml of LiBH4. The mixture is allowed to return to ambient temperature and 1 ml of 2N NaOH is added. The reaction medium is evaporated to dryness. Water is added, and the medium is acidified with 1N HCl and extracted with EtOAc. The organic phase is evaporated to dryness. The product is triturated in water, filtered, and washed with water. The product is taken up in methanol and evaporated to dryness.

Workup

  1. temperatureThe mixture is refluxed
  2. temperatureThe mixture is refluxed for 20 hours
  3. customto return to ambient temperature
  4. customThe reaction medium is evaporated to dryness
  5. additionWater is added
  6. extractionextracted with EtOAc
  7. customThe organic phase is evaporated to dryness
  8. customThe product is triturated in water
  9. filtrationfiltered
  10. washwashed with water
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-3f9a75cf07254c26b0d086e40965d442
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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