Potassium Carbonate → 5-[4-(1-Hydroxy-1-methylethyl)phenyl]-2-[(6-methoxy-1,5-naphthyridin-2-yl)amino]thiophene-3-carboxamide

HRID 1799574Notes

Reaction equation

HRID 1799574 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[N:8]=2)[N:3]=1.[NH2:14][C:15]1[S:16][C:17]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([OH:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=2)=[CH:18][C:19]=1[C:20]([NH2:22])=[O:21].C(=O)([O-])[O-].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:32][C:29]([C:26]1[CH:25]=[CH:24][C:23]([C:17]2[S:16][C:15]([NH:14][C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[N:8]=4)[N:3]=3)=[C:19]([C:20]([NH2:22])=[O:21])[CH:18]=2)=[CH:28][CH:27]=1)([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 582166512-Bromo-6-methoxy-1,5-naphthyridineHCID 595262122-Amino-5-[4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide

Product 1

HCID 445551285-[4-(1-Hydroxy-1-methylethyl)phenyl]-2-[(6-methoxy-1,5-naphthyridin-2-yl)amino]thiophene-3-carboxamide

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The title compound was prepared according to the general procedure in Example 30 (Method B) using 2-bromo-6-methoxy-1,5-naphthyridine (54 mg, 0.22 mmol), 2-amino-5-[4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide (60 mg, 0.20 mmol), potassium carbonate (31 mg, 0.22 mmol), X-Phos (49 mg, 0.10 mmol), and tris(dibenzylideneacetone)dipalladium (16 mg, 0.02 mmol) as the starting materials.

Sources & evidence

ORD record
ord-64fc27bc05be44fa8a78d89842dfa7ac
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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