Sodium borohydride → HCID 58382115, compound

HRID 1628085Notes

Reaction equation

HRID 1628085 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[N:12]=[C:13]3[CH:19]=[CH:18][N:17]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[C:14]3=[N:15][CH:16]=2)=[NH:10])=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:11]2[N:12]=[C:13]3[CH:19]=[CH:18][N:17]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:21])=[O:22])[C:14]3=[N:15][CH:16]=2)[NH2:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58382290HCID 58382290, compound

Product 1

HCID 58382115HCID 58382115, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask was added (4-methoxyphenyl)(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanimine (1.36 g, 3.35 mmol, Preparation #AF.1) and NaBH4 (0.127 g, 3.35 mmol) in MeOH (20 mL). The mixture was stirred for about 30 min at rt. The mixture was concentrated in vacuo, DCM (10 mL) was added to the residue and the insoluble material was removed via filtration. The filtrate was loaded on a 40 g silica column and product was eluted with 50 to 100% EtOAc/DCM to provide (4-methoxyphenyl)(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.595 g, 44%): 1H NMR (d-DMSO) δ 8.56 (s, 1H), 8.29-8.24 (m, 1H), 8.02-7.96 (m, 2H), 7.43 (dd, J=8.3, 0.9 Hz, 2H), 7.36-7.31 (m, 2H), 6.96 (d, J=4.1 Hz, 1H), 6.84 (m, 2H), 5.22 (s, 1H), 3.68 (s, 3H), 2.33 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo, DCM (10 mL)
  2. additionwas added to the residue
  3. customthe insoluble material was removed via filtration
  4. washwas eluted with 50 to 100% EtOAc/DCM

Sources & evidence

ORD record
ord-4a1ccd2e25da46179d7b7b5958feb296
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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