Potassium Carbonate → HCID 86674546, compound

HRID 1851958Notes

Reaction equation

HRID 1851958 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.C([O-])([O-])=O.[K+].[K+].[C:50](B1OC(C)(C)C(C)(C)O1)([CH3:52])=[CH2:51]>O1CCOCC1.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:42][C:17]1[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[C:30]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:25][CH:24]=2)[C:19]2[C:15]([C:16]=1[CH3:43])=[CH:14][C:13]([C:11](=[O:12])[NH:10][C@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:50]([CH3:52])=[CH2:51])[CH:3]=1)[CH3:9])=[CH:21][CH:20]=2

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 71075173HCID 71075173, compound

Product 1

HCID 86674546HCID 86674546, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A solution of (S)-tert-butyl 4′-((5-((1-(3-bromophenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylate (83 mg, 0.13 mmol, 1 equiv.), K2CO3 (36 mg, 0.26 mmol, 2 equiv.) and Pd(PPh3)4 (15 mg, 0.013 mmol, 0.1 equiv.) in dioxane/water (1.2 mL/0.3 mL) was degassed with argon. The isopropenylboronic acid pinacol ester (49 μL, 0.26 mmol, 2 equiv.) was added and the solution was heated at 100° C. for 1 h under microwave irradiation. The resulting solution was diluted with ethyl acetate, washed with a 0.5 N HCl solution, saturated aqueous NaHCO3 and brine, and then dried over Na2 SO4. The obtained oil was used without further purification. ESI-MS (m/z): 599 [M+H]+.

Workup

  1. washwashed with a 0.5 N HCl solution, saturated aqueous NaHCO3 and brine
  2. customdried over Na2 SO4
  3. customThe obtained oil was used without further purification

Sources & evidence

ORD record
ord-38782c410bd4412494363ed7afdb5018
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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