5-Bromo-N-methylpyridin-2-amine → 5-[1,3]Dioxolo[4,5-f][1,3]benzothiazol-6-yl-N-methylpyridin-2-amine

HRID 1698103Notes

Reaction equation

HRID 1698103 reaction equation
[O:1]1[C:12]2[C:4](=[CH:5][C:6]3[S:10][CH:9]=[N:8][C:7]=3[CH:11]=2)[O:3][CH2:2]1.Br[C:14]1[CH:15]=[CH:16][C:17]([NH:20][CH3:21])=[N:18][CH:19]=1.COC1N=CC(C2SC3C=CC=CC=3N=2)=CN=1>[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[O:1]1[C:12]2[C:4](=[CH:5][C:6]3[S:10][C:9]([C:14]4[CH:15]=[CH:16][C:17]([NH:20][CH3:21])=[N:18][CH:19]=4)=[N:8][C:7]=3[CH:11]=2)[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 156456635-Bromo-N-methylpyridin-2-amineHCID 20557021[1,3]Dioxolo[4',5':4,5]benzo[1,2-d]thiazoleHCID 248037262-(2-Methoxypyrimidin-5-yl)-1,3-benzothiazole

Product 1

HCID 248043995-[1,3]Dioxolo[4,5-f][1,3]benzothiazol-6-yl-N-methylpyridin-2-amineYield 35.7%

Reagents, catalysts & solvents 1

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)Catalyst

Conditions

Temperature
170 °C

Procedure

To [1,3]Dioxolo[4,5-f][1,3]benzothiazole (98 mg, 0.55 mmol) and 5-bromo-N-methylpyridin-2-amine (112 mg, 0.60 mmol) were subjected to the procedure used for the preparation of 2-(2-methoxypyrimidin-5-yl)-1,3-benzothiazole, with the following exceptions: 5 mol % bis(tri-t-butylphosphine) palladium (0) was used and the reaction was heated under argon at 170° C. in a microwave oven for 30 min. The crude material was purified by flash chromatography (Heptane/EtOAc 1:1) to give the title compound (56 mg) as a yellow solid. 1H NMR δ 8.62 (d, 1H) 7.94 (dd, 1H) 7.61 (s, 1H) 7.47 (s, 1H) 7.19 (q, 1H) 6.57 (d, 1H) 6.13 (s, 2H) 2.85 (d, 3H); MS m/z (M+H) 286.

Workup

  1. customThe crude material was purified by flash chromatography (Heptane/EtOAc 1:1)

Sources & evidence

ORD record
ord-568de3695f204747b080debcad9088a0
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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