Potassium Carbonate → 7-Bromo-6-(3-fluorophenyl)-1,2-benzothiazole

HRID 389579Notes

Reaction equation

HRID 389579 reaction equation
[Br:1][C:2]1[C:10]2[S:9][N:8]=[CH:7][C:6]=2[CH:5]=[CH:4][C:3]=1I.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].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.O>[Br:1][C:2]1[C:10]2[S:9][N:8]=[CH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([F:12])[CH:18]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27339863-Fluorophenylboronic acidHCID 667602837-Bromo-6-iodo-1,2-benzothiazole

Product 1

HCID 667606767-Bromo-6-(3-fluorophenyl)-1,2-benzothiazoleYield 60.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A suspension of 7-bromo-6-iodo-1,2-benzothiazole (29.6 mg, 0.0871 mmol), 3-fluorobenzeneboronic acid (12.8 mg, 0.0915 mmol), potassium carbonate (39.2 mg, 0.284 mmol), and Pd(PPh3)4 (12.2 mg, 0.0106 mmol) in 4:1 1,4-dioxane:water (1 mL) was heated to 80° C. for 15 h. The reaction mixture was concentrated in vacuo. Purification of the residue by ISCO chromatography (0 to 100% dichloromethane:heptane) to afford 16.2 mg (59%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 9.08 (s, 1H), 7.73 (d, J=7.58 Hz, 1H), 7.52 (dt, J=5.81, 7.96 Hz, 1H), 7.37 (qd, J=0.88, 7.71 Hz, 1H), 7.33 (d, J=7.58 Hz, 1H), 7.28-7.31 (m, 1H), 7.20 (ddt, J=1.01, 2.59, 8.43 Hz, 1H); MS (ESI): 307.87, 309.86 [M+H]+; HPLC tR=4.33 min (ZQ3: nonpolar—5 min).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification of the residue by ISCO chromatography (0 to 100% dichloromethane:heptane)

Sources & evidence

ORD record
ord-e81f841c1cb3476a8b8ff578acd890e0
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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