Dimethylformamide → 2-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

HRID 1851759Notes

Reaction equation

HRID 1851759 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9](OC)[CH:8]=[CH:7][C:5]=2[N:6]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[CH:23][C:24](N)=[N:25][CH:26]=2)O1.[C:29]([O-:32])([O-])=O.[K+].[K+].C(OCC)(=O)C.C[N:42](C=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:29][O:32][C:24]1[N:25]=[CH:26][C:21]([C:2]2[S:3][C:4]3[CH:10]=[C:9]([NH2:42])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 112187652-Bromo-6-methoxy-1,3-benzothiazole

Product 1

HCID 248035652-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-6-methoxy-benzothiazole (1.14 g), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (1.23 g, 1.2 eq.), Pd(dppf)Cl2*DCM (170 mg, 0.05 eq.) and 2.0 M aq. K2CO3 (10 ml, 4 eq.) in DMF (20 ml) was heated at 80° C. for 2 h under argon while stirring. Ethyl acetate (200 ml) was subsequently added before concentrating the sol. onto diatomaceous earth in vacuo. Purification by flash chromatography (DCM:methanol, 99:1 to 95:5) provided the title compound (730 mg) as a yellow solid. 1H NMR δ 8.56 (d, 1 H) 7.96 (dd, 1 H) 7.82 (d, 1 H) 7.64 (d, 1 H) 7.07 (dd, 1 H) 6.67 (br. s, 2 H) 6.55 (d, 1 H) 3.83 (s, 3 H); MS m/z (M+H) 258.1.

Workup

  1. concentrationbefore concentrating the sol. onto diatomaceous earth in vacuo
  2. customPurification by flash chromatography (DCM:methanol, 99:1 to 95:5)

Sources & evidence

ORD record
ord-2c5a9b73acdb47fe8b2b767d01190f93
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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