Triphenylphosphine → HCID 53237707, compound

HRID 640707Notes

Reaction equation

HRID 640707 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:19](NOC4CCCCO4)=[O:20])[C:15]([CH2:16][CH2:17][OH:18])=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[C:10](=[C:15]4[CH2:16][CH2:17][O:18][C:19](=[O:20])[C:14]4=[N:13][CH:12]=3)[CH:9]=[CH:8]2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 53237708HCID 53237708, compound

Product 1

HCID 53237707HCID 53237707, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-(4-fluorobenzyl)-4-(2-hydroxyethyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxamide (0.16 g, 0.39 mmol) and triphenylphosphine (0.12 g, 0.46 mmol) in THF (10 mL), was added dropwise diisopropylazodicarboxylate (0.09 mL, 94 mg, 0.46 mmol) in THF (1 mL) was added. The resulting mixture was stirred at room temperature for 1 hour, and the solvent was evaporated. Purification by Biotage chromatography provided 0.12 g of a crude material that was used without further purification in the next step. LCMS (APCl, M+H+): 396.2.

Workup

  1. additionwas added
  2. customthe solvent was evaporated
  3. customPurification by Biotage chromatography

Sources & evidence

ORD record
ord-20f1d2b65deb49a0b706fd50c38a18df
Source dataset
uspto-grants-2010_04
Patent number
US07692014B2

Reaction notes

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