2-Bromo-1,3-benzothiazole → HCID 87378836, compound

HRID 1470990Notes

Reaction equation

HRID 1470990 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C@H:10]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24].Br[C:27]1[S:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C@H:10]2[CH2:11][CH2:12][C@H:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:23]([O-:25])=[O:24])[CH:4]=3)[N:9]2[C:27]2[S:28][C:29]3[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=3[N:31]=2)=[CH:14][C:15]=1[N+:20]([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 6120402-Bromo-1,3-benzothiazoleHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 86649111HCID 86649111, compound

Product 1

HCID 87378836HCID 87378836, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The product from Example 115B (0.335 g, 0.877 mmol), 2-bromobenzo[d]thiazole (0.281 g, 1.32 mmol), tris(dibenzylideneacetone)dipalladium(0) 0.08 g (0.088 mmol), BINAP (0.055 g, 0.088 mmol), and sodium tert-butoxide (0.126 g, 1.32 mmol) were combined in dioxane (8 mL) and nitrogen was bubbled through the solution for 10 minutes. The tube was sealed and heated at 100° C. for 18 hours. The reaction mixture was partitioned between brine and dichloromethane and the organics were concentrated and purified by combi-flash 24 g silica column, eluting with 1:1 hexanes: dichloromethane, followed by 100% dichloromethane to give 0.165 g (37%) of the title compound.

Workup

  1. customnitrogen was bubbled through the solution for 10 minutes
  2. customThe tube was sealed
  3. customThe reaction mixture was partitioned between brine and dichloromethane
  4. concentrationthe organics were concentrated
  5. custompurified by combi-flash 24 g silica column
  6. washeluting with 1:1 hexanes

Sources & evidence

ORD record
ord-0c4a90f0b4714f5fb4fe9827f09b6c7a
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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