Benzo(B)Thiophene-2-Boronic Acid → (6-Benzo[b]thiophen-2-yl-2-methoxy-pyrimidin-4-yl)-[2-(4-methoxy-phenyl)-ethyl]-amine

HRID 216110Notes

Reaction equation

HRID 216110 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:3]=1.[S:21]1[C:25](B(O)O)=[CH:24][C:23]2[CH:29]=[CH:30][CH:31]=[CH:32][C:22]1=2.C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>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.C1CCCCC1>[S:21]1[C:25]([C:2]2[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:3]=2)=[CH:24][C:23]2[CH:29]=[CH:30][CH:31]=[CH:32][C:22]1=2

Participants

7

Reactant 4

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 57636025(6-Chloro-2-methoxy-pyrimidin-4-yl)-[2-(4-methoxyphenyl)-ethyl]amine

Product 1

HCID 53323184(6-Benzo[b]thiophen-2-yl-2-methoxy-pyrimidin-4-yl)-[2-(4-methoxy-phenyl)-ethyl]-amineYield 42.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8078CyclohexaneSolvent

Procedure

By proceeding in a similar manner as above in Example 10(a) but using (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(4-methoxy-phenyl)-ethyl]-amine (150 mg), benzo[b]thiophene-2-boronic acid (182 mg), Cs2CO3 (590 mg) and tetrakis(triphenylphosphine)palladium (0) (58 mg), and subjecting the crude reaction product to flash column chromatography on silica gel eluting with a mixtures of 20 to 100% EtOAc and cyclohexane, there is prepared (6-benzo[b]thiophen-2-yl-2-methoxy-pyrimidin-4-yl)-[2-(4-methoxy-phenyl)-ethyl]-amine [85 mg, 42% yield, Example 10(g)]. LCMS: RT=10.39 minutes, MS: 392 (M+H). IC50=5.1 nM

Sources & evidence

ORD record
ord-542fa3dded734d5aa796435027c19aa6
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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