2-Chlorobenzothiazole → HCID 24804238, compound

HRID 1698097Notes

Reaction equation

HRID 1698097 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C[Sn](C)(C)[C:13]1[CH:14]=[CH:15][C:16]([C:19]([NH2:21])=[O:20])=[N:17][CH:18]=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>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[C:13]1[CH:14]=[CH:15][C:16]([C:19]([NH2:21])=[O:20])=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 119872-ChlorobenzothiazoleHCID 57553399HCID 57553399, compound

Product 1

HCID 24804238HCID 24804238, compoundYield 29.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-chloro-1,3-benzothiazole (38 μL, 0.31 mmol), 5-(trimethylstannyl)pyridine-2-carboxamide (97 mg, 0.34 mmol) and Pd(PPh3)4 (35 mg, 0.03 mmol) in dry dioxane (2 mL) was heated under argon to 160° C. for 30 min in a microwave reactor. The precipitate was filtered off. Flash chromatography (DCM/MeOH 99:1→DCM/Acetone 1:1) gave the title compound (23 mg) as a white solid. 1H NMR δ 9.31 (dd, 1H) 8.63 (dd, 1H) 8.27 (br s, 1H) 8.26-8.19 (m, 2H) 8.16 (d, 1H) 7.83 (br s, 1H) 7.64-7.59 (m, 1H) 7.57-7.52 (m, 1H); MS m/z (M+H) 256.

Workup

  1. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-299ecfbc39d14a0ab391cab504964aa6
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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