Benzyl Bromide → HCID 69491442, compound

HRID 1296754Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([O:33][CH3:34])[C:31]=1[CH3:32])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]=[C:19]([CH3:21])[O:18][N:17]=2)=[CH:12][C:11]=1[NH:22][C:23](=O)[C:24](F)(F)F)=[O:7].C(Br)[C:36]1[CH:41]=[CH:40]C=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:23]([NH:22][C:11]1[CH:12]=[C:13]([C:16]2[N:20]=[C:19]([CH3:21])[O:18][N:17]=2)[CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:31]([CH3:32])=[C:30]([O:33][CH3:34])[CH:29]=1)[C:24]1[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of compound 1h (200 mg, 0.42 mmol), benzyl bromide (0.100 mL, 0.84 mmol), and potassium carbonate (173 mg, 1.25 mmol) in DMF (2 mL) was sealed in a pressure tube and heated at 60° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with water, dried, and concentrated on a rotary evaporator. The residue was dissolved in a mixture of MeOH (10 mL) and water (1 mL), and potassium carbonate (200 mg) was added. The reaction mixture was stirred at rt overnight. The reaction mixture was diluted with water and the precipitated solid was recovered by filtration and dried in vacuo to give compound 23a (163 mg, 82%). ESI-MS m/e 473.1 (M+1).

Workup

washwashed with water
customdried
concentrationconcentrated on a rotary evaporator
dissolutionThe residue was dissolved in a mixture of MeOH (10 mL) and water (1 mL), and potassium carbonate (200 mg)
additionwas added
additionThe reaction mixture was diluted with water
filtrationthe precipitated solid was recovered by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-c54c207e84df43378fc7c1c34497ca26
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07247654B2

Reaction notes

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