Potassium Phosphate, Tribasic → HCID 49819733, compound

HRID 1623562Notes

Reaction equation

HRID 1623562 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9](B3OC(C)(C)C(C)(C)O3)=[CH:10][C:5]=2[S:4][C:3]1=[O:20].Br[C:22]1[CH:23]=[C:24]([NH2:28])[CH:25]=[N:26][CH:27]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:28][C:24]1[CH:23]=[C:22]([C:9]2[CH:8]=[CH:7][C:6]3[N:2]([CH3:1])[C:3](=[O:20])[S:4][C:5]=3[CH:10]=2)[CH:27]=[N:26][CH:25]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 8176813-Amino-5-bromopyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 59535313HCID 59535313, compound

Product 1

HCID 49819733HCID 49819733, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3-Methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-benzothiazol-2-one (873.5 mg, 3 mmol), 5-Bromo-pyridin-3-ylamine (519 mg, 3 mmol), Pd2(dba)3 (24.7 mg, 0.06 mmol), S—PHOS (62 mg, 0.15 mmol), K3PO4 (1.27 g, 6 mmol) in toluene (15 mL) was heated to 95° C. for overnight. After filtration, concentration, the residue was purified by flash column (MeOH/CH2Cl2, v/v, 1.5-3%) and yielded yellow solid (380 mg). MS (ESI) m/z 258.0 (M+H)+. 1H NMR (400 MHz, CDCl3) δ ppm 3.49 (s, 3H), 3.78 (brs, 2H), 7.10-7.12 (m, 1H), 7.12 (s, 1H), 7.51 (dd, J=8, 2 Hz, 1H), 7.60 (d, J=2 Hz, 1H), 8.08 (d, J=2.6 Hz, 1H), 8.23 (d. J=2 Hz, 1H).

Workup

  1. filtrationAfter filtration, concentration
  2. customthe residue was purified by flash column (MeOH/CH2Cl2, v/v, 1.5-3%)

Sources & evidence

ORD record
ord-1084746901e74f5aac19ffaf76fd254d
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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