Water → 2-Amino-5-(3-hydroxymethyl-phenyl)-N-pyridin-4-yl-nicotinamide

HRID 919242Notes

Reaction equation

HRID 919242 reaction equation
[NH2:1][C:2]1[N:16]=[CH:15][C:14](Br)=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:5].[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:27]([O-])([O-])=[O:28].[Na+].[Na+].O>CN(C=O)C.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[NH2:1][C:2]1[N:16]=[CH:15][C:14]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([CH2:27][OH:28])[CH:19]=2)=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 621554162-amino-5-bromo-N-(pyridin-4-yl)nicotinamide

Product 1

HCID 710610312-Amino-5-(3-hydroxymethyl-phenyl)-N-pyridin-4-yl-nicotinamide

Reagents, catalysts & solvents 2

HCID 178477754HCID 178477754, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

100 mg of 2-amino-5-bromo-N-pyridin-4-yl-nicotinamide and 62.2 mg 3-hydroxy-methyl)-benzeneboronic acid are dissolved in 4 ml of DMF. 90.4 mg Na2CO3 and 1 ml water are added under argon. 13.9 mg of [1,1-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) are added. The mixture is stirred for 14 h at 100° C.

Sources & evidence

ORD record
ord-dbbd538c1f8c43d28b3a2ce2852a0936
Source dataset
uspto-grants-2016_03
Patent number
US09273029B2

Reaction notes

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