Triphenylphosphine → HCID 58382158, compound

HRID 1628047Notes

Reaction equation

HRID 1628047 reaction equation
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([CH:20]=[N:21][C:22]=3[C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.O[CH:64]1[CH2:68][CH2:67][N:66]([C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[CH2:65]1>C1COCC1>[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([CH:20]=[N:21][C:22]=3[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH:68]4[CH2:64][CH2:65][N:66]([C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[CH2:67]4)=[CH:25][CH:24]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 44169391-Boc-3-pyrrolidinolHCID 5363146Diisopropyl azodicarboxylateHCID 136175008HCID 136175008, compound

Product 1

HCID 58382158HCID 58382158, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenol (0.1 g, 0.247 mmol, Prepared using AF from Preparation #AE.1 with (4-tert-butoxyphenyl)magnesium bromide [Novel], AG, J.3 with ethyl formate and L.2 with POCl3) and PPh3 (0.10 g, 0.40 mmol) in THF (1 mL) was added DIAD (0.077 mL, 0.40 mmol). The mixture was stirred at rt for about 20 min and tert-butyl 3-hydroxypyrrolidine-1-carboxylate (0.058 g, 0.31 mmol) was added. The mixture was stirred at rt for about 20 h and the mixture was purified directly by silica gel (25 g) chromatography eluting with a gradient of 40 to 90% EtOAc/DCM to afford tert-butyl 3-(4-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenoxy)pyrrolidine-1-carboxylate (0.14 g, 100%): LC/MS (Table 2, Method c) Rt=1.51 min; MS m/z 574 (M+H)+.

Workup

  1. stirringThe mixture was stirred at rt for about 20 h
  2. customthe mixture was purified directly by silica gel (25 g) chromatography
  3. washeluting with a gradient of 40 to 90% EtOAc/DCM

Sources & evidence

ORD record
ord-2828088f40dc4342baf71e254114725f
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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