4-Bromophenacyl bromide → HCID 69673289, compound

HRID 1751335Notes

Reaction equation

HRID 1751335 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[C:17]([OH:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1)=[O:23].CCN(CC)CC>CC#N.CCOC(C)=O.C([O-])(O)=O.[Na+].[Cl-].[Na+].O>[N:8]1([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[C:17]([O:19][CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1)=[O:23])=[O:18]

Participants

8

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 8471TriethylamineHCID 2755955(2S)-1-(tert-Butoxycarbonyl)-2,3-dihydro-1H-indole-2-carboxylic acid

Product 1

HCID 69673289HCID 69673289, compound

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (S)-1-(tert-butoxycarbonyl)indoline-2-carboxylic acid (1.61 g, 6.11 mmol) and 2-bromo-1-(4-bromophenyl)ethanone (2.55 g, 9.17 mmol) in MeCN (25 mL) was added Et3N (1.27 mL, 9.17 mmol). The solution was heated to 55° C. and stirred o/n. The solution was cooled to rt, diluted with EtOAc, sat. NaHCO3, brine, dried with MgSO4, and concentrated. The residue was taken onto the next step crude.

Workup

  1. temperatureThe solution was cooled to rt
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-066fd6372ed14d02b08e01ff46a81305
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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