Lithium Chloride → HCID 86700462, compound

HRID 879648Notes

Reaction equation

HRID 879648 reaction equation
Br[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:19]([O:21][CH3:22])=[O:20])[C:8]([CH3:28])=[CH:7][C:5]=2[N:6]=1.[CH3:29][N:30]1[C:38]2[C:33](=[N:34][C:35]([Sn](CCCC)(CCCC)CCCC)=[CH:36][CH:37]=2)[C:32]([N:52]2[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]2)=[N:31]1.[Li+].[Cl-]>O1CCOCC1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:24]([O:23][C@@H:18]([C:9]1[C:8]([CH3:28])=[CH:7][C:5]2[N:6]=[C:2]([C:35]3[N:34]=[C:33]4[C:32]([N:52]5[CH2:53][CH2:54][N:55]([CH3:58])[CH2:56][CH2:57]5)=[N:31][N:30]([CH3:29])[C:38]4=[CH:37][CH:36]=3)[S:3][C:4]=2[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:19]([O:21][CH3:22])=[O:20])([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 86699809Methyl (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetateHCID 86700463HCID 86700463, compound

Product 1

HCID 86700462HCID 86700462, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (S)-methyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (22 mg, 0.046 mmol) in dioxane (2 mL), was added 1-methyl-3-(4-methylpiperazin-1-yl)-5-(tributylstannyl)-1H-pyrazolo[4,3-b]pyridine (20 mg, 0.038 mmol), CuI (7 mg, 0.038 mmol), LiCl (8 mg, 0.19 mmol) and Pd(PPh3)4 (4.4 mg, 0.004 mmol). The reaction mixture was heated at 100° C. for 2 h. The reaction was cooled, washed with sat. NaHCO3, extracted with EtOAc, dried over MgSO4, filtered, concentrated down and purified by silica gel column, first eluting by 0-100% EtOAc in hexanes, then eluting by 0-20% MeOH in dichloromethane to give the product. LCMS-ESI+: calc'd for C33H37ClN6O3S: 633.2 (M+H+); Found: 633.3 (M+H+).

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with sat. NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. custompurified by silica gel column
  8. washfirst eluting by 0-100% EtOAc in hexanes
  9. washeluting by 0-20% MeOH in dichloromethane
  10. customto give the product

Sources & evidence

ORD record
ord-17a5129059f84b5fa267d673a0ef90ed
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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