Potassium Phosphate, Tribasic → HCID 71496744, compound

HRID 1750401Notes

Reaction equation

HRID 1750401 reaction equation
Br[C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([NH:19][CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:18])[N:15]=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:7]([N:6]1[C:2]([C:32]2[CH:33]=[CH:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=2)=[C:3]([C:11]2[S:12][CH:13]=[C:14]([CH2:16][C:17]([NH:19][CH2:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:18])[N:15]=2)[CH:4]=[N:5]1)([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 201262(4-Methoxyphenyl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86721244HCID 86721244, compound

Product 1

HCID 71496744HCID 71496744, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A solution of the compound (100 mg, 0.23 mmol) obtained in step 8, 4-methoxyphenylboronic acid (51.6 mg, 0.34 mmol), tripotassium phosphate (96 mg, 0.45 mmol), S-Phos (6.51 mg, 0.02 mmol) and palladium(II) acetate (1.8 mg, 8.02 μmol) in toluene (1.5 mL) was stirred under an argon atmosphere at 90° C. for 18 hr. The reaction mixture was purified by silica gel column chromatography (solvent gradient; 50% ethyl acetate/hexane→5% methanol/ethyl acetate) to give the title compound (55 mg, 0.117 mmol, 52%) as a white powder.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (solvent gradient; 50% ethyl acetate/hexane→5% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-ad088c9ecae8421ca5f7938bf2ce23b9
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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