Acetic Acid → 3-(3-Hydroxymethylphenyl)-1,6-dimethyl-1,9-dihydro-2H-pyrido[2,3-b]indol-2-one

HRID 133188Notes

Reaction equation

HRID 133188 reaction equation
[CH3:1][N:2]1[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH:5]=[C:4]([C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=2)[CH:19]=[O:20])[C:3]1=[O:24])=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=3.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[OH:20][CH2:19][C:18]1[CH:17]=[C:16]([C:4]2[C:3](=[O:24])[N:2]([CH3:1])[C:7]3[NH:8][C:9]4[C:14]([C:6]=3[CH:5]=2)=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=4)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 866023433-(1,6-Dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]-indol-3-yl)benzaldehyde

Product 1

HCID 673870523-(3-Hydroxymethylphenyl)-1,6-dimethyl-1,9-dihydro-2H-pyrido[2,3-b]indol-2-oneYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

280 mg of the compound obtained in Stage A are placed in 10 ml of CH2Cl2 and the minimum amount of AcOH to dissolve the compound, 375 mg of NaBH(OAc)3 are added and then the mixture is left stirring at AT for 18 hours. The reaction medium is evaporated and the residue is taken up in AcOEt and then filtration is carried out to produce 200 mg of the expected compound.

Workup

  1. additionare added
  2. waitthe mixture is left
  3. customThe reaction medium is evaporated
  4. filtrationfiltration

Sources & evidence

ORD record
ord-dd37dfd8276044ac8aeefb8ec0f2bc04
Source dataset
uspto-grants-2008_06
Patent number
US07390818B2

Reaction notes

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