Potassium Carbonate → HCID 67333061, compound

HRID 1672254Notes

Reaction equation

HRID 1672254 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)O1.[C:17]([O:21][C:22](=[O:43])[CH:23]([NH:33][C:34](=[O:42])[C:35]1[CH:40]=[CH:39][C:38](Br)=[CH:37][CH:36]=1)[CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([CH3:20])([CH3:19])[CH3:18].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.CCCCCC>COCCOC.O.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>[C:17]([O:21][C:22](=[O:43])[CH:23]([NH:33][C:34]([C:35]1[CH:36]=[CH:37][C:38]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)=[CH:39][CH:40]=1)=[O:42])[CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([CH3:18])([CH3:19])[CH3:20]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 21226206Ethyl acetate hexaneHCID 67331755HCID 67331755, compound

Product 1

HCID 67333061HCID 67333061, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (1.34 g, 6.104 mmol, 1 equiv.) and 2-(4-Bromo-benzoylamino)-pentanedioic acid di-tert-butyl ester (2.7 g, 6.104 mmol, 1 equiv.) were dissolved in DME (120 mL). A solution of K2CO3 (1.68 g, 12.21 mmol, 2 equiv.) in 30 mL of water was injected into the mixture, followed by the addition of Pd(PPh3)4 (352 mg, 0.31 mmol, 5%). The mixture was heated to reflux overnight. Reaction was complete as determined by TLC. Regular work-up and column chromatography (silica gel, 30-40% EtOAc/n-Hexane) afforded 2.3 g of 2-[(4′-Amino-biphenyl-4-carbonyl)-amino]-pentanedioic acid di-tert-butyl ester in 83% yield. MS (ESI) m/z 453.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customReaction

Sources & evidence

ORD record
ord-6c798ba68025483f81f500a182423621
Source dataset
uspto-grants-2011_08
Patent number
US07998965B2

Reaction notes

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