Potassium Carbonate → HCID 86705046, compound

HRID 1477921Notes

Reaction equation

HRID 1477921 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)([CH2:11][CH3:12])[CH:9]=O)=[CH:4][CH:3]=1.[C:30]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)([CH2:11][CH3:12])[C:9]#[CH:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86705043HCID 86705043, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86705046HCID 86705046, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of tert-butyl (1-(2-(4-chlorophenyl)-1-oxobutan-2-yl)-1H-indol-4-yl)carbamate (412 mg, 1 mmol), as described in Example 21 Step B, and K2CO3 (276 mg, 2 mmol) in methanol (10 mL) was added dimethyl 1-diazo-2-oxopropylphosphonate (230 mg, 1.2 mmol) at room temperature. The mixture was stirred for 2 h and the solid was filtered off and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with PE/EA (20/1 to 10/1, v/v) to give the title compound as colorless amorphous solid. LC/MS m/z=352.9[M-tBu+H]+.

Workup

  1. filtrationthe solid was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with PE/EA (20/1 to 10/1

Sources & evidence

ORD record
ord-58a4542c3c9d4ae9b4382247e12f9e92
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

Loading…