Triphenylphosphine → HCID 178481627, compound

HRID 707294Notes

Reaction equation

HRID 707294 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[C:12]([O:16][C:17](=[O:24])[NH:18][C@H:19]1[CH2:22][C@H:21](O)[CH2:20]1)([CH3:15])([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C([O-])(O)=O.[Na+]>[C:12]([O:16][C:17](=[O:24])[NH:18][C@H:19]1[CH2:20][C@H:21]([N:4]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:10]3[N:2]([CH3:1])[C:3]2=[O:11])[CH2:22]1)([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 8542361-Methyl-1h-imidazo[4,5-b]pyridin-2(3h)-oneHCID 178454126HCID 178454126, compound2×

Product 1

HCID 178481627HCID 178481627, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (9.63 g, 64.6 mmol), tert-butyl(trans-3-hydroxycyclobutyl)carbamate (Intermediate 69, 12.1 g, 64.6 mmol), and triphenylphosphine (25.4 g, 97 mmol) were mixed in THF (250 mL) under an argon atmosphere at 0° C. Diisopropyl azodicarboxylate (19.0 mL, 97 mmol) was added dropwise via syringe, and the reaction mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was diluted with saturated NaHCO3 and extracted with EtOAc (3×). The organic layer was separated, washed with brine, dried over MgSO4, filtered, and concentrated. The resulting crude product was purified via silica gel flash column chromatography eluting with 0 to 100% EtOAc in hexanes to yield the title compound as a yellow solid and used in the next step without further purification.

Workup

  1. extractionextracted with EtOAc (3×)
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude product was purified via silica gel flash column chromatography
  8. washeluting with 0 to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-9888337a74364b0e8e90bbb38fd9efe2
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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