Diisopropylamine → S-1-(4-Fluorophenyl)-1H-indazol-5-yl benzothioate

HRID 1661465Notes

Reaction equation

HRID 1661465 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13](I)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[C:18]([OH:26])(=[S:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.C(NC(C)C)(C)C>C1(C)C=CC=CC=1.CCOC(C)=O.[I+].[Cu+]>[C:18](=[O:26])([S:25][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[N:9]=[CH:10]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 592511281-(4-fluorophenyl)-5-iodo-1H-indazoleHCID 178526132HCID 178526132, compound

Product 1

HCID 59339848S-1-(4-Fluorophenyl)-1H-indazol-5-yl benzothioateYield 20%

Reagents, catalysts & solvents 3

HCID 178505377HCID 178505377, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-5-iodo-1H-indazole (0.224 g, 0.66 mmol), thiobenzoic acid (0.093 ml, 0.79 mmol), 3,4,7,8-tetramethyl-1,10-phenantroline (0.031 g, 0.13 mmol) and N,N-diisopropylamine (0.220 ml, 1.32 mmol) in toluene (2.5 ml) was added copper(I) iodine (2.245 μl, 0.07 mmol). The resulting mixture was stirred at 110C O/N. The reaction mixture was cooled to rt diluted with EtOAc and washed with water. The organic phase was the dried the solvent evaporated and then purified on HPLC. The relevant fractions were collected freeze dried to give 45 mg (20%) of product which was analysed by LC/MS.

Workup

  1. washwashed with water
  2. customdried the solvent
  3. customevaporated
  4. custompurified on HPLC
  5. customThe relevant fractions were collected freeze
  6. customdried

Sources & evidence

ORD record
ord-4687a533b68344feaf8a6231339f05e6
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

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