1-Phenylethanol → HCID 66699709, compound

HRID 388129Notes

Reaction equation

HRID 388129 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]([CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:12])[C:9](=[O:19])[N:8](C(OC(C)(C)C)=O)[C:5]2=[N:6][CH:7]=1.Br[C:28]1[CH:29]=[C:30]2NC(=O)N(C(OCCCC)=O)[C:31]2=[N:32][CH:33]=1.[C:45]1(C(O)C)[CH:50]=CC=[CH:47][CH:46]=1.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>O1CCCC1>[C:13]1([CH:11]([N:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:47]4[CH:46]=[CH:45][CH:50]=[C:31]5[C:30]=4[CH:29]=[CH:28][CH:33]=[N:32]5)[CH:3]=3)[NH:8][C:9]2=[O:19])[CH3:12])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 74091-PhenylethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66699891tert-Butyl 6-bromo-2-oxo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyridine-3(2H)-carboxylateHCID 86658263HCID 86658263, compound

Product 1

HCID 66699709HCID 66699709, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 6-bromo-2-oxo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyridine-3(2H)-carboxylate. To a solution of tent-butyl 6-bromo-2-oxo-1H-imidazo[4,5-b]pyridine-3(2H)-carboxylate (See Example 166.C) (0.60 g, 1.97 mmol), 1-phenylethanol (0.289 g, 2.37 mmol) and triphenylphosphine (0.62 g, 2.37 mmol) in tetrahydrofuran (15 mL) was added diisopropyl azodicarboxylate (0.46 mL, 2.37 mmol). After stirring at room temperature for 1 h, the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography to afford the title compound (0.30 g, 36% yield). MS (ESI) m/z 418.2 [M+1]+.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-33ac96e566d841d388711236c8c802e8
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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