1,4-Dioxane → HCID 86700439, compound

HRID 879630Notes

Reaction equation

HRID 879630 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][CH:12]=[C:13]([Sn](CCCC)(CCCC)CCCC)[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Br[C:29]1[S:30][C:31]2[C:37]([C:38]3[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=3)=[C:36]([C@H:45]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[C:46]([O:48][CH3:49])=[O:47])[C:35]([CH3:55])=[CH:34][C:32]=2[N:33]=1.O1CCOCC1>C(OCC)(=O)C.[F-].[Na+].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:51]([O:50][C@@H:45]([C:36]1[C:35]([CH3:55])=[CH:34][C:32]2[N:33]=[C:29]([C:13]3[N:14]=[C:10]([N:7]4[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]4)[S:11][CH:12]=3)[S:30][C:31]=2[C:37]=1[C:38]1[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=1)[C:46]([O:48][CH3:49])=[O:47])([CH3:54])([CH3:52])[CH3:53]

Participants

8

Reactant 3

HCID 312751,4-DioxaneHCID 86699809Methyl (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetateHCID 86700440HCID 86700440, compound

Product 1

HCID 86700439HCID 86700439, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 5235Sodium FluorideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A 5 mL microwave reaction tube was charged with 2-(4-isopropylpiperazin-1-yl)-4-(tributylstannyl)thiazole (33 mg, 0.066 mmol), (S)-methyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (40 mg, 1.2 eq.), Pd(PPh3)4 (15 mg, 15 mol %), CuI (5 mg, 30 mol %) and dioxane (1 mL). The reaction was heated to 110° C. in oil bath for 1 hour. Reaction mixture was diluted with ethyl acetate and saturated NaF aqueous solution was added and stirred for 30 minutes. Extracted with ethyl acetate and the organic layer was concentrated and purified via Combiflash (0-100% ethyl acetate in hexane) to give desired compound. LCMS-ESI+: calc'd for C31H38ClN4O3S2: 613.2 (M+H+); Found: 613.4 (M+H+).

Workup

  1. customReaction mixture
  2. additionwas added
  3. extractionExtracted with ethyl acetate
  4. concentrationthe organic layer was concentrated
  5. custompurified via Combiflash (0-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b57e5172bcc942a3ac4de5c0f4802338
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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