1,1'-Carbonyldiimidazole → HCID 59425244, compound

HRID 907171Notes

Reaction equation

HRID 907171 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]([CH2:22][CH3:23])[C:11]3[C:16]([C:17]=2[C:18]#[N:19])=[CH:15][CH:14]=[C:13]([O:20][CH3:21])[CH:12]=3)[CH:5]=[CH:6][C:7]=1[OH:8].C1N=CN([C:29](N2C=NC=C2)=[O:30])C=1>C1COCC1>[CH2:22]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:20][CH3:21])[CH:12]=2)[C:17]([C:18]#[N:19])=[C:9]1[C:4]1[CH:5]=[CH:6][C:7]2[O:8][C:29](=[O:30])[NH:1][C:2]=2[CH:3]=1)[CH3:23]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59425699HCID 59425699, compound

Product 1

HCID 59425244HCID 59425244, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

2-(3-Amino-4-hydroxyphenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (100 mg, 0.33 mmol), prepared as in step A, was combined with CDI (83 mg, 0.51 mmol), and THF (1.1 mL). This was heated at 65° C. for 1 hour. The reaction mixture was partitioned between EtOAc and aqueous HCl. The organic layer was dried and concentrated. Purification by silica gel chromatography (9/1, CH2Cl2/EtOAc) yielded 1-ethyl-6-methoxy-2-(2-oxo-2,3-dihydro-benzooxazol-5-yl)-1H-indole-3-carbonitrile (89 mg, 81%) as a white solid.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and aqueous HCl
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (9/1, CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-f91ec6479b234194ba38eb815b9cad4b
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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