Lithium Chloride → HCID 86700466, compound

HRID 879653Notes

Reaction equation

HRID 879653 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]([C:52]2[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=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]([C:52]5[CH:53]=[N:54][CH:55]=[CH:56][CH: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 86700467HCID 86700467, compound

Product 1

HCID 86700466HCID 86700466, 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 (8 mg, 0.018 mmol) in dioxane (2 mL), was added 1-methyl-3-(pyridin-3-yl)-5-(tributylstannyl)-1H-pyrazolo[4,3-b]pyridine (9 mg, 0.018 mmol), CuI (3.4 mg, 0.018 mmol), LiCl (3.8 mg, 0.09 mmol) and Pd(PPh3)4 (2 mg, 0.002 mmol). The reaction mixture was heated at 100° C. for 2 h. The reaction was cooled, washed with sat. NaHCO3, extracted by EtOAc, dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting with 0-100% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C33H30ClN5O3S: 612.2 (M+H+); Found: 612.2 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-7e2b141c859640b4822205590ca79c1d
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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