Methanesulfonyl chloride → (cis-1-(benzyl(methyl)amino)-7-bromo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-2-yl)methyl methanesulfonate

HRID 1481800Notes

Reaction equation

[CH2:1]([N:8]([CH3:24])[C@@H:9]1[C:13]2=[CH:14][C:15]3[CH:16]=[C:17]([Br:21])[CH:18]=[CH:19][C:20]=3[N:12]2[CH2:11][C@@H:10]1[CH2:22][OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[CH3:34][S:35]([O:23][CH2:22][C@H:10]1[CH2:11][N:12]2[C:20]3[CH:19]=[CH:18][C:17]([Br:21])=[CH:16][C:15]=3[CH:14]=[C:13]2[C@H:9]1[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:24])(=[O:37])=[O:36]

Participants

Conditions

Temperature: 0 °C

Procedure

The product from Step 2 (690 mg, 1.8 mmol) was dissolved in CH2Cl2 (10 mL) with N,N-diisopropylethylamine (0.94 mL, 5.4 mmol). The mixture was cooled to 0° C., before adding methanesulfonyl chloride (0.21 mL, 2.7 mmol). After 30 min, the mixture was washed with water, dried over Na2SO4 and concentrated. The crude mixture was carried on without further purification.

Workup

washthe mixture was washed with water
dry with materialdried over Na2SO4
concentrationconcentrated
customThe crude mixture was carried on without further purification

Sources & evidence

ORD record: ord-2d72b4e0bf1d4622aaf346998e1c1f79
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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