Lithium Chloride → HCID 86700337, compound

HRID 879518Notes

Reaction equation

HRID 879518 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:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=2[N:6]=1.[Cl-].[Li+].[CH3:32][N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:44]=[N:43][CH:42]=[C:41]([Sn](CCCC)(CCCC)CCCC)[N:40]=2)[CH2:35][CH2:34]1>O1CCOCC1.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.[Cu]I>[C:25]([O:24][C@@H:18]([C:9]1[C:8]([CH3:29])=[CH:7][C:5]2[N:6]=[C:2]([C:41]3[CH:42]=[N:43][CH:44]=[C:39]([N:36]4[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]4)[N:40]=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][CH2:22][CH3:23])=[O:20])([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetateHCID 86700338HCID 86700338, compound

Product 1

HCID 86700337HCID 86700337, 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
90 °C

Procedure

(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (50.0 mg, 0.101 mmol), tetrakis(triphenylphosphine)palladium(0) (17.4 mg, 0.015 mmol), lithium chloride (12.8 mg, 0.302 mmol), and copper(I) iodide (5.8 mg, 0.030 mmol) were taken in a microwave vial and the vial vacuum pumped and flushed with argon three times. To this mixture was added 2-(4-methylpiperazin-1-yl)-6-(tributylstannyl)pyrazine (56.4 mg, 0.121 mmol) in dioxane (1.0 mL), and the resulting mixture was stirred at 90° C. for 22 h. Purification by flash column chromatography on silica gel using 79:20:1 DCM/MeOH/NH3 (0 to 100%) in DCM provided the product. LCMS-ESI+ calc'd for C31H37ClN5O3S (M+H+):594.2; Found: 593.6 (M+H+).

Workup

  1. customflushed with argon three times
  2. customPurification by flash column chromatography on silica gel using 79:20:1 DCM/MeOH/NH3 (0 to 100%) in DCM
  3. customprovided the product

Sources & evidence

ORD record
ord-659418d89e904efaa962a0ce18960a7b
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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