Triphenylphosphine → HCID 118079038, compound

HRID 1485733Notes

Reaction equation

HRID 1485733 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Br:15][C:16]1[CH:21]=[C:20]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:19]([NH:33][C@@H:34]([CH3:37])[CH2:35]O)=[CH:18][N:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:15][C:16]1[N:17]=[CH:18][C:19]2[NH:33][C@@H:34]([CH3:37])[CH2:35][N:22]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:20]=2[CH:21]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 118079730HCID 118079730, compound

Product 1

HCID 118079038HCID 118079038, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Diisopropyl azodicarboxylate (0.013 ml, 0.066 mmol) was added dropwise to a 60° C. solution of (S)-N-(2-bromo-5-(1-hydroxypropan-2-ylamino)pyridin-4-yl)-4-methylbenzene sulfonamide (0.022 g, 0.055 mmol) and triphenylphosphine (0.017 g, 0.066 mmol) in THF (1.0 mL). The reaction mixture stirred at 60° C. for 10 min. The mixture was concentrated and the residue was purified via column chromatography on silica gel (Biotage 10 g column, gradient elution with 0-50% ethyl acetate-hexane) to afford (S)-7-bromo-3-methyl-1-tosyl-1,2,3,4-tetrahydropyrido[4,3-b]pyrazine (0.013 g, 62%) as a light purple solid. MS (ESI, pos. ion) m/z 382, 384.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified via column chromatography on silica gel (Biotage 10 g column, gradient elution with 0-50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ee9d77fa427c4991a4f0625bdd63f766
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

Loading…