Dichloromethane → 3-(3-Chlorophenyl)-2,6-dimethylthieno[2,3-b]pyridin-4-amine

HRID 573543Notes

Reaction equation

Br[C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][C:7]([CH3:12])=[N:6][C:5]=2[S:4][C:3]=1[CH3:13].[Cl:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.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].O>[Cl:14][C:15]1[CH:20]=[C:19]([C:2]2[C:10]3[C:9]([NH2:11])=[CH:8][C:7]([CH3:12])=[N:6][C:5]=3[S:4][C:3]=2[CH3:13])[CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Under nitrogen, 3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-amine (170 mg, 0.661 mmol) (Description 8) was dissolved in toluene (6 mL) and (3-chlorophenyl)boronic acid (155 mg, 0.992 mmol), PdCl2(dppf).DCM (54.0 mg, 0.066 mmol) and Cs2CO3 (646 mg, 1.983 mmol) were added and the mixture heated in a microwave at 150° C. for 30 min. The reaction mixture was combined with the material (30 mg) from similar reaction. Water (20 mL) was added and the mixture extracted with ethyl acetate (3×15 mL). The organic layer was dried over MgSO4, filtered and solvent removed in vacuo. Purification by chromatography on silica gel, eluting with a gradient of 0-50% ethyl acetate in cyclohexane, afforded the title compound (204.4 mg). LCMS (A) m/z: 291 [M+1]+, Rt 0.84 min (acidic).

Workup

extractionthe mixture extracted with ethyl acetate (3×15 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customsolvent removed in vacuo
customPurification by chromatography on silica gel
washeluting with a gradient of 0-50% ethyl acetate in cyclohexane

Sources & evidence

ORD record: ord-a16e56a030414cecbdba2da572508c5e
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029545B2

Reaction notes

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