Pyrrolidine → HCID 68464959, compound

HRID 501201Notes

Reaction equation

HRID 501201 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:31][CH2:30][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[CH:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][CH:23]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH:46]1[CH2:50][CH2:49][CH2:48][CH2:47]1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]2[CH2:31][CH2:30][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[CH:27]=[CH:26][C:25]([CH2:28][N:46]6[CH2:50][CH2:49][CH2:48][CH2:47]6)=[CH:24][CH:23]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 58703310HCID 58703310, compound

Product 1

HCID 68464959HCID 68464959, compoundYield 176.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of Example 102 (1.0 g, 2.42 mmol) in DCM (50 mL) was added Na(OAc)3BH (1.028 g, 4.8 mmol) and stirred for 10 min. To the reaction mixture was added pyrrolidine (0.861 g, 12.13 mmol) under nitrogen atmosphere and the reaction mixture was continued stirring at room temperature for 4 hr. The progress of the reaction was monitored by TLC and upon completion of the reaction the mixture was partitioned between DCM (100 mL) and water (15 mL) and the organic layer was separated, washed with water (2×10 mL), dried over sodium sulfate filtered and the solvent was removed under reduced pressure to give crude residue, which was purified by column chromatography using silica gel to provide methyl-2-{8-[4-(pyrrolidin-1-ylmethyl)phenyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (2 g, 95%).

Workup

  1. stirringthe reaction mixture was continued stirring at room temperature for 4 hr
  2. customThe progress of the reaction was monitored by TLC and upon completion of the reaction the mixture
  3. customwas partitioned between DCM (100 mL) and water (15 mL)
  4. customthe organic layer was separated
  5. washwashed with water (2×10 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customto give crude residue, which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-dce3c415e5c44b66983c076da81222fc
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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