Benzyl Bromide → HCID 18385446, compound

HRID 1250214Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH2:22][CH2:23][N:24]2[C:32](=[O:33])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]2=[O:34])[CH:13]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:45](Br)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH2:22][CH2:23][N:24]2[C:32](=[O:33])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]2=[O:34])[CH:13]=1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -10 °C

Procedure

2-(N-tert-butoxycarbonylamino)-1-{1-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propyl]-3-indolyl}-1-ethanone (0.30 g, 0.65 mmol) was dissolved in dry THF (7.5 ml) and cooled to −10° C., sodium bis(trimethylsilyl)amide (0.65 ml, 1 M in THF, 0.65 mmol) was added and the resulting yellow solution stirred for 15 minutes. Benzylbromide (0.16 ml, 1.30 mmol) was added and the stirring continued for 15 minutes at −10° C., the cooling bath was removed and stirring continued for 4 hours. Saturated NH4Cl(aq) was added followed by removal of the aqueous phase. The organic solvent was evaporated in vacuum and the residue chromatographed furnishing the sub-title product (0.28 g, 79%).

Workup

waitthe stirring continued for 15 minutes at −10° C.
customthe cooling bath was removed
stirringstirring
waitcontinued for 4 hours
additionSaturated NH4Cl(aq) was added
customfollowed by removal of the aqueous phase
customThe organic solvent was evaporated in vacuum
customthe residue chromatographed

Sources & evidence

ORD record: ord-7006479d7fb340edab1de7312c296e95
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337342B1

Reaction notes

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