Dichloromethane → HCID 44125548, compound

HRID 558075Notes

Reaction equation

HRID 558075 reaction equation
[Br:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([Cl:17])[CH:16]=2)[C:12]#[N:13])=[C:6]([F:18])[C:5]([CH2:19][C:20]2[C:28]3[C:23](=[N:24][N:25]=[CH:26][CH:27]=3)[N:22]([CH2:29][OH:30])[N:21]=2)=[CH:4][CH:3]=1.C(Cl)Cl.[C:34](OC(=O)C)(=[O:36])[CH3:35]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:19][C:20]2[C:28]3[C:23](=[N:24][N:25]=[CH:26][CH:27]=3)[N:22]([CH2:29][O:30][C:34](=[O:36])[CH3:35])[N:21]=2)=[C:6]([F:18])[C:7]=1[O:8][C:9]1[CH:10]=[C:11]([C:12]#[N:13])[CH:14]=[C:15]([Cl:17])[CH:16]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic Anhydride2×HCID 67000936HCID 67000936, compound

Product 1

HCID 44125548HCID 44125548, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 12 (0.1 g, 0.2 mmol) and DCM (3 mL) was added pyridine (0.08 mL, 1.0 mmol) and acetic anhydride (612 mg, 6 mmol). The resulting solution was stirred overnight at RT under an inert atmosphere. Starting material was still evident and additional aliquots of pyridine (0.08 mL) and Ac2O (0.612 g) were added and the resulting mixture stirred at 55° C. for ca. 5 h. The volatile contents were evaporated and the residue purified in two batches on a preparative SiO2 TLC plate developed with 60% EtOAc/hexane containing 1% TEA. The product was eluted from the plate and crystallized from DCM/hexane to afford 0.076 g of I-8: Anal. Calcd. for C22H14BrClFN5O3: C, 49.79; H, 2.66; N, 13.20. Found: C, 49.87; H, 2.63; N, 12.92.

Workup

  1. stirringthe resulting mixture stirred at 55° C. for ca. 5 h
  2. customThe volatile contents were evaporated
  3. customthe residue purified in two batches on a preparative SiO2 TLC plate
  4. washThe product was eluted from the plate
  5. customcrystallized from DCM/hexane
  6. customto afford 0.076 g of I-8: Anal

Sources & evidence

ORD record
ord-b63ce9fa30e04fbbaeb6c0006803a2e9
Source dataset
uspto-grants-2011_11
Patent number
US08063028B2

Reaction notes

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