Dichloromethane → HCID 68172804, compound

HRID 713988Notes

Reaction equation

HRID 713988 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[F:24][C:25]([F:38])([F:37])[CH:26]1[CH2:31][CH2:30][CH:29](OS(C)(=O)=O)[CH2:28][CH2:27]1.ClCCl>CC(O)(C)C.CC(=O)CC>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH:29]3[CH2:30][CH2:31][CH:26]([C:25]([F:38])([F:37])[F:24])[CH2:27][CH2:28]3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 10657398N-Boc-5-HydroxyindolineHCID 86668431HCID 86668431, compound

Product 1

HCID 68172804HCID 68172804, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (0.33 g, 1.4 mmol), cesium carbonate (0.93 g, 2.8 mmol), and methanesulfonic acid 4-trifluoromethyl-cyclohexyl ester (0.70 g, 2.8 mmol) in t-BuOH (5 mL) and 2-butanone (2.5 mL) was heated in a sealed vial at 100° C. overnight. The mixture was treated with dichloromethane to form precipitate. The solid was filtered off and the filtrate was concentrated. The residue was treated with minimum of amount dichloromethane to form solid during 2 days. The solid was filtered and washed with ether to give desired product (200 mg, yield: 40%). ESI-MS: 408.20 (M+23)+.

Workup

  1. customto form precipitate
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate was concentrated
  4. additionThe residue was treated with minimum of amount dichloromethane
  5. customto form solid during 2 days
  6. filtrationThe solid was filtered
  7. washwashed with ether

Sources & evidence

ORD record
ord-41f2680e557f44d88e0c20981204afae
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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