Benzyl Bromide → HCID 66913617, compound

HRID 2104571Notes

Reaction equation

HRID 2104571 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[C:21]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][C:34]([OH:36])=[O:35])=[CH:29][CH:28]=3)[CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:37])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[C:21]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH:33]([CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:34]([OH:36])=[O:35])=[CH:29][CH:28]=3)[CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:37])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 23648472HCID 23648472, compound

Product 1

HCID 66913617HCID 66913617, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (4-{[3-(3-benzoyl-8-methyl-quinolin-4-yl)-phenylamino]-methyl}-phenyl)-acetic acid (0.04 g, 0.08 mmol), benzyl bromide (0.12 g, 0.8 mmol), and cesium carbonate (0.33 g, 1 mmol) in 5 mL of DMF was stirred at room temperature for 2 h. The reaction was quenched with water and extracted with ethyl acetate. The combined organics were washed with water, dried over magnesium sulfate and concentrated. The crude ester was treated with LiOH followed by semi-preparative HPLC purification to give the title compound. MS (ESI) m/z 577.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. additionThe crude ester was treated with LiOH
  7. customfollowed by semi-preparative HPLC purification

Sources & evidence

ORD record
ord-67745b95324044ec97eb39cd99fd80d4
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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