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Lithium Chloride → HCID 86700281, compound

HRID 879551
Notes
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Reaction equation

HRID 879551 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([Sn](CCCC)(CCCC)CCCC)[S:5][CH:6]=1.Br[C:21]1[S:22][C:23]2[C:29]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)=[C:28]([C@H:37]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:27]([CH3:48])=[CH:26][C:24]=2[N:25]=1.[Li+].[Cl-]>O1CCOCC1.CCOC(C)=O.[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>[Br:1][C:2]1[N:3]=[C:4]([C:21]2[S:22][C:23]3[C:29]([C:30]4[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=4)=[C:28]([C@H:37]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:27]([CH3:48])=[CH:26][C:24]=3[N:25]=2)[S:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 433294Lithium ChlorideHCID 110486874-Bromo-2-(tributylstannyl)thiazoleHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Product 1

HCID 86700281HCID 86700281, compound

Reagents, catalysts & solvents 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418397HCID 178418397, compoundCatalyst
HCID 8857Ethyl AcetateSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 10 mL reaction vial, 4-bromo-2-(tributylstannyl)thiazole (125 mg, 0.251 mmol) and (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (114 mg, 0.251 mmol) were dissolved in dioxane (3 mL) at room temperature under argon atmosphere. The solution was bubbled with argon for 5 min. Then CuI (10.6 mg, 0.055 mmol), LiCl (31.7 mg, 0.753 mmol) and Pd(PPh3)4 (52.3 mg, 0.0417 mmol) were added sequentially. The reaction mixture was then sealed and heated in oil bath at 100° C. for 3.5 h. The reaction mixture was then diluted with EtOAc (10 mL), filtered and the filtrate was concentrated and purified on silica gel column with 0-10% EtOAc/Hex to afford title compound. LCMS-ESI+: calc'd for: C25H24BrClN2O3S2: 581.0, 579.0, 582.0, 583.0, 580.0 (M+H+); found: 581.1, 579.0, 582.2, 583.1, 580.3 (M+H+).

Workup

  1. customIn a 10 mL reaction vial
  2. customThe solution was bubbled with argon for 5 min
  3. customThe reaction mixture was then sealed
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. custompurified on silica gel column with 0-10% EtOAc/Hex

Sources & evidence

ORD record
ord-fdffbdbf952c4172a9ff8ad17d7a2888
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987250B2

Reaction notes

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