Diazomethane → HCID 18379010, compound

HRID 2299008Notes

Reaction equation

HRID 2299008 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]=[CH:14][C:15]1[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=1)[CH2:21][N:20]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19][CH2:18]3)[CH:7]=[CH:6]2)#[N:2].[N+](=[CH2:34])=[N-]>C1COCC1.C(OCC)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]1[CH2:34][CH:14]1[C:15]1[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=1)[CH2:21][N:20]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19][CH2:18]3)[CH:7]=[CH:6]2)#[N:2]

Participants

6

Reactant 2

HCID 9550Diazomethane3×HCID 69561113HCID 69561113, compound

Product 1

HCID 18379010HCID 18379010, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst3×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 42I (207 mg, 0.5 mmol) and Pd(OAc)2 (5 mg) in THF (100 mL), at 0° C. was treated with a 0° C. 2M solution of diazomethane in diethyl ether (20 mL), warmed to room temperature over 10 minutes, treated with Pd(OAc)2 (5 mg) and 2M diazomethane in diethyl ether (20 mL), and treated two more times with Pd(OAc)2 and 2M diazomethane after 10 minute stirring intervals. After the final addition, the mixture was stirred for 1 hour, filtered through diatomaceous earth (Celite®) and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes to provide the desired product.

Workup

  1. additionAfter the final addition
  2. stirringthe mixture was stirred for 1 hour
  3. filtrationfiltered through diatomaceous earth (Celite®)
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-39bebdde98c84cb087557c1a3e9d539c
Source dataset
uspto-grants-2002_12
Patent number
US06495562B1

Reaction notes

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