Water → HCID 71099680, compound

HRID 1852040Notes

Reaction equation

HRID 1852040 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@@H:8]([NH:10][C:11]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]4[C:30]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:25][CH:24]=2)[C:17]([CH3:42])=[C:16]3[CH3:43])=[O:12])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH:44]1(B(O)O)[CH2:46][CH2:45]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:44]1([C:2]2[CH:3]=[C:4]([C@@H:8]([NH:10][C:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]5[C:30]([C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=5)=[CH:27][CH:28]=3)[C:17]([CH3:42])=[C:16]4[CH3:43])=[O:12])[CH3:9])[CH:5]=[CH:6][CH:7]=2)[CH2:46][CH2:45]1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 71075173HCID 71075173, compound

Product 1

HCID 71099680HCID 71099680, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of (S)-tert-butyl 4′-((5-((1-(3-bromophenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylate (24 mg, 0.038 mmol), cyclopropylboronic acid (7 mg, 0.081 mmol), Palladium(II) acetate (3.5 mg, 0.016 mmol) tricyclohexylphosphine (9 mg, 0.032 mmol) and potassium phosphate, tribasic, (23 mg, 0.11 mmol) in toluene (0.7 mL) and water (0.07 mL) was heated at 100° C. for 1 h in a Biotage Microwave reactor. The solvent was removed; the residue was filtered and purified by preparative HPLC to yield the title compound as a white solid.

Workup

  1. customThe solvent was removed
  2. filtrationthe residue was filtered
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-7ef6f4abdf8d414eaace0aef7e04b29b
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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