Borane → HCID 21196140, compound

HRID 1066794Notes

Reaction equation

HRID 1066794 reaction equation
Cl[C:2]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:3]=1[O:4][CH2:5][C:6]1[N:7]([CH3:28])[C:8]2[C:13]([C:14]=1[C:15](=[O:27])C(N(C)C1CCN(C)CC1)=O)=[CH:12][CH:11]=[CH:10][CH:9]=2.B.[CH2:35]1[CH2:39]O[CH2:37][CH2:36]1>>[Cl:33][C:31]1[CH:30]=[CH:29][C:3]([O:4][CH2:5][C:6]2[N:7]([CH3:28])[C:8]3[C:13]([C:14]=2[CH:15]([OH:27])[CH2:8][N:7]2[CH2:6][CH2:5][CH:35]([CH3:39])[CH2:36][CH2:37]2)=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:2][CH:32]=1

Participants

4

Reactant 3

HCID 6331BoraneHCID 8028TetrahydrofuranHCID 21196018HCID 21196018, compound

Product 1

HCID 21196140HCID 21196140, compound

Procedure

Under a nitrogen atmosphere a round bottom flask was charged with 2-[(2,4-dichlorophenoxy)methyl]-1-methyl-3-[2-[N-methyl-N-(1-methylpiperidin-4-yl)amino]-1,2-ethanedionyl]-1H-indole (0.3349 g, 0.686 mmol) and placed in an ice bath Borane-tetrahydrofuran complex (4.11 ml of a 1.0 M borane solution in THF, 4.11 mmol) was added slowly and the ice bath was removed. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was stirred for about one hour and then 0.33 ml of a 1:1 tetrahydrofuran:methanol solution was added. Sodium hydroxide (1.74 ml of a 5.0 N solution) was then added and the resulting mixture was heated to reflux and maintained at this temperature overnight.

Workup

  1. customplaced in an ice bath
  2. customthe ice bath was removed
  3. addition0.33 ml of a 1:1 tetrahydrofuran:methanol solution was added
  4. additionSodium hydroxide (1.74 ml of a 5.0 N solution) was then added
  5. temperaturethe resulting mixture was heated
  6. temperatureto reflux
  7. temperaturemaintained at this temperature overnight

Sources & evidence

ORD record
ord-b7b369a3496c463492470b85c263bb1f
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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