Potassium Iodide → HCID 68840237, compound

HRID 1726104Notes

Reaction equation

HRID 1726104 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][CH:30]=[C:29]([O:34][CH2:35][CH2:36]Br)[CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].[K+].[CH2:47]([NH:49][CH2:50][CH3:51])[CH3:48].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[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][CH:30]=[C:29]([O:34][CH2:35][CH2:36][N:49]([CH2:50][CH3:51])[CH2:47][CH3:48])[CH:28]=3)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8021DiethylamineHCID 10796Cesium carbonateHCID 68838881HCID 68838881, compound

Product 1

HCID 68840237HCID 68840237, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound 5-benzyloxy-3-[1-tert-butoxycarbonyl-6-(2-diethylaminoethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester is prepared according to procedure N using 1.23 g of 5-benzyloxy-3-[6-(2-bromoethoxy)-1-tert-butoxycarbonyl-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester, 50 ml of acetonitrile, 401 mg of potassium iodide, 204 mg of diethylamine, and 770 mg of cesium carbonate. After treatment, the reaction crude is purified by chromatography on a cartridge of 20 g of silica; eluent: 98/2, 95/5, 92/8 dichloromethane/methanol to obtain 390 mg of 5-benzyloxy-3-[1-tert-butoxycarbonyl-6-(2-diethylaminoethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe compound 5-benzyloxy-3-[1-tert-butoxycarbonyl-6-(2-diethylaminoethoxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester is prepared
  2. customAfter treatment, the reaction crude
  3. customis purified by chromatography on a cartridge of 20 g of silica

Sources & evidence

ORD record
ord-67521ab4f4444709b9ae17ea6cb4b3eb
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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