Boron tribromide → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1698083Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17](OC)[CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][N:5]=1)C.B(Br)(Br)Br.[C:25]([O-])(O)=[O:26].[Na+]>ClCCl>[CH3:25][O:26][C:16]1[CH:17]=[CH:18][C:12]2[S:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]([NH:3][CH3:1])=[N:5][CH:6]=3)=[N:14][C:13]=2[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To N-ethyl-5-(6-methoxy-1,3-benzothiazol-2-yl)pyridin-2-amine (52.8 mg, 0.185 mmol) in dichloromethane (2 mL) was added BBr3 in dichloromethane (1 M, 925 μL) at 0° C. under an argon atmosphere. The reaction was then stirred at 0° C. for 3 h before it was neutralized with NaHCO3 (sat aq). The precipitated product was filtered off, washed with water and DCM and dried. Recrystallization from (MeOH/toluene) gave the title compound (11 mg) as a white solid. 1H NMR δ ppm 9.75 (br s, 1H) 8.58 (d, 1H) 7.93 (dd, 1H) 7.73 (d, 1H) 7.34 (d, 1H) 7.19 (t, 1H) 6.92 (dd, 1H) 6.56 (d, 1H) 3.32-3.38 (m, 2H) 1.16 (t, 3H); MS m/z (M+H) 272.

Workup

filtrationThe precipitated product was filtered off
washwashed with water and DCM
customdried
customRecrystallization from (MeOH/toluene)

Sources & evidence

ORD record: ord-2bdf6359bda346ef86f2aa7678beeb83
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163928B2

Reaction notes

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