Potassium Iodide → HCID 57562498, compound

HRID 1726098Notes

Reaction equation

HRID 1726098 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([O:34][CH2:35][CH2:36]Br)=[CH:29][CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].[K+].[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.ClCCl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[C:10]([C:25]2[N:26]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([O:34][CH2:35][CH2:36][N:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)=[CH:29][CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium Iodide2×HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 57562451HCID 57562451, compound

Product 1

HCID 57562498HCID 57562498, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

2.0 g of 5-benzyloxy-3-[5-(2-bromoethoxy)-1-tert-butoxycarbonyl-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester are stirred in 90 ml of acetonitrile. 498 mg of potassium iodide are added and the suspension is heated to 80° C. After 7 h 20 min, the following reactants are successively added: 394 μl of morpholine, 1.24 g of potassium carbonate, 150 mg of potassium iodide. The suspension is heated at 80° C. overnight. The insoluble material is filtered off and the filtrate is concentrated under vacuum. The reaction crude is taken up in 50 ml of dichloromethane. The organic phase is washed with 2 times 25 ml of distilled water. The organic phase is dried over magnesium sulfate and filtered. The solvent is evaporated off in a rotary evaporator to obtain 1.90 g of 5-benzyloxy-3-[1-tert-butoxycarbonyl-5-(2-morpholin-4-ylethoxy)-1H-indol-2-yl]-indazole-1-carboxylic acid tert-butyl ester.

Workup

  1. additionthe following reactants are successively added
  2. temperatureThe suspension is heated at 80° C. overnight
  3. filtrationThe insoluble material is filtered off
  4. concentrationthe filtrate is concentrated under vacuum
  5. customThe reaction crude
  6. washThe organic phase is washed with 2 times 25 ml of distilled water
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent is evaporated off in a rotary evaporator

Sources & evidence

ORD record
ord-fa49a94c044845f485d67a893215a0cf
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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