Sodium Carbonate → Isobutyl-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-amine

HRID 1665032Notes

Reaction equation

HRID 1665032 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][NH:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[CH3:13][S:14]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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].ClCCl>[CH2:9]([NH:8][CH2:7][C:5]1[S:6][C:2]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([S:14]([CH3:13])(=[O:16])=[O:15])[CH:22]=2)=[CH:3][CH:4]=1)[CH:10]([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 28428595N-[(5-Bromothiophen-2-yl)methyl]-2-methylpropan-1-amine

Product 1

HCID 67441398Isobutyl-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-amine

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

In analogy to example 1, step 3, (5-bromo-thiophen-2-ylmethyl)-isobutyl-amine was reacted with (3-methylsulfonylphenyl)-boronic acid, Na2CO3 and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct in dioxane/water to give isobutyl-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-amine as a light yellow oil. MS: 324.3 ([M+H]+)

Sources & evidence

ORD record
ord-27e3082b015047ce8608dce4bb77cd16
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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