Sodium borohydride → HCID 68283194, compound

HRID 624039

Reaction equation

HRID 624039 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][CH:11]=O)[CH:8]=1)([O-:3])=[O:2].[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH2:19][CH2:18]2.[BH4-].[Na+]>CO>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:11][CH2:10][CH2:9][N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[N:6]1)[CH2:19][CH2:18]2

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 107019745-methoxy-2,3-dihydro-1H-indoleHCID 63041126HCID 63041126, compound

Product 1

HCID 68283194HCID 68283194, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(4-nitro-1H-pyrazol-1-yl)propanal (200 mg, 1.18 mmol) in MeOH (12.0 mL), 5-methoxyindoline (176 mg, 1.18 mmol) was added. This reaction mixture was stirred at rt for 1 h, then NaBH4 (121 mg, 3.20 mmol) was added and stirred for another 30 min at rt. The reaction mixture was quenched with water and extracted with EtOAc (2×). The combined org. layers were dried (MgSO4), filtered and the solvent was removed under reduced pressure to yield 5-methoxy-1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)indoline, which was used in the next step without further purification. LC-MS conditions B: tR=0.56 min, [M+H]+=303.15.

Workup

  1. stirringstirred for another 30 min at rt
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EtOAc (2×)
  4. dry with materiallayers were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cde93af1e38f40169d633bab2c6659cf
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Linked notes

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