Tributylphosphine → HCID 59375030, compound

HRID 661823Notes

Reaction equation

HRID 661823 reaction equation
[Br:1][C:2]1[C:3]([CH3:21])=[C:4]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][C:11]=2[CH2:18]O)[CH:5]=[CH:6][CH:7]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C(P(CCCC)CCCC)CCC>C1COCC1>[Br:1][C:2]1[C:3]([CH3:21])=[C:4]([N:8]2[C:9](=[O:20])[C:10]3[C:11](=[CH:12][CH:13]=[C:14]([C:16]#[N:17])[CH:15]=3)[CH2:18]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 66605859HCID 66605859, compound

Product 1

HCID 59375030HCID 59375030, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 2 A solution of N-(3-bromo-2-methylphenyl)-5-cyano-2-(hydroxymethyl)benzamide (170 mg, 0.492 mmol) in THF (20 mL) was treated with di-tert-butyl azodicarboxylate (113 mg, 0.492 mmol) and tributylphosphine (0.119 mL, 0.492 mmol) and stirred at rt. After 2 h the mixture was concentrated and the residue was column chromatography (eluting with a gradient from 90:10 to 50:50 hexane-EtOAc) to provide 2-(3-bromo-2-methylphenyl)-3-oxoisoindoline-5-carbonitrile (100 mg, 62%) as a white solid. 1H NMR (400 MHz, chloroform-d) δ 8.07 (1H, d, J=8.1 Hz), 7.82-7.89 (2H, m), 7.64 (1H, dd, J=7.8, 1.4 Hz), 7.13-7.25 (2H, m), 4.78 (2H, s), 2.30 (3H, s). Mass spectrum m/z 327, 329 (M+H)+.

Workup

  1. concentrationAfter 2 h the mixture was concentrated
  2. washeluting with a gradient from 90:10 to 50:50 hexane-EtOAc)

Sources & evidence

ORD record
ord-d4a2777b29c84c6b93e4ef7f5d8e28e3
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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