HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

4-Bromobenzoic acid → 4-[(2-Carbamoylethyl)amino]benzoic acid

HRID 590
Notes
Print preview

Reaction equation

HRID 590 reaction equation
Cl.NCCC(N)=O.O=C(O)c1ccc(Br)cc1>C1CCCC1.C1CCOC1.CC(=O)O.CC(=O)O.CC(C1CCCC1P(C1CCCCC1)C1CCCCC1)P(C(C)(C)C)C(C)(C)C.C[Si](C)(C)[N-][Si](C)(C)C.[Fe].[Li+].[Pd]>NC(=O)CCNc1ccc(C(=O)O)cc1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 114644-Bromobenzoic acidHCID 222222883-Aminopropanamide hydrochloride

Product 1

HCID 622313754-[(2-Carbamoylethyl)amino]benzoic acidYield 0%

Reagents, catalysts & solvents 4

HCID 2733832Lithium hexamethyldisilazaneReagentHCID 4144353Palladium (II) acetateCatalyst
HCID 144543273
(R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene, 1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-, (2R)-
Catalyst
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Palladium (II) acetate (0.011 g, 0.05 mmol) was added to(R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (0.027 g, 0.05 mmol) in THF (1 mL) in a reaction vessel evacuated and purged with nitrogen. The resulting catalyst mixture was stirred and under nitrogen at 50 °C for 30 minutes. 04-Dec-2013 10:52:28 AM -0500 LiHMDS (1.194 mL, 1.19 mmol), 3-aminopropanamide, HCl (0.077 g, 0.62 mmol) and 4-bromobenzoic acid (0.1 g, 0.50 mmol) was added to a second reaction vessel and purged with nitrogen. were added at 20 °C. The catalyst solution was added to the reaction mixture and the resulting mixture was stirred at 120 °C for 16 hours. LCMS showed starting material only. Desired product not isolated from this reaction.

Sources & evidence

ORD record
ord-f95171c2975240019dea4c87294370ec
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureSources & evidenceReaction notes