Iodoethane → HCID 70562026, compound

HRID 1427214Notes

Reaction equation

[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][N:23]2[CH:29]([C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[C:30]([O:32][CH3:33])=[O:31])=[O:17])([CH3:14])([CH3:13])[CH3:12].I[CH2:42][CH3:43]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[C:11]([O:15][C:16]([NH:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][N:23]2[C:29]([C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)([CH2:42][CH3:43])[C:30]([O:32][CH3:33])=[O:31])=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: -78 °C

Procedure

LiHMDS (20 mL, 0.020 mol) was added dropwise to a stirred solution of methyl 2-(4-(tert-butoxycarbonylamino)-6-fluoro-1H-indol-1-yl)-2-(4-chlorophenyl)acetate (4.32 g, 0.010 mol) in THF (80 mL) and HMPA (20 mL) at −78° C. The resulting mixture was stirred for another 1 h at −78° C. Iodoethane (2.3 g, 0.015 mol) was added to the above solution. The reaction mixture was warmed to −20° C. and stirred for 20 min. The mixture was quenched with sat. ammonium chloride and extracted with EA, washed with brine and dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel flash chromatography (PE:EA=8:1) to afford the title compound. LC/MS m/z=405.1 [M-tBu+H]+.

Workup

temperatureThe reaction mixture was warmed to −20° C.
stirringstirred for 20 min
customThe mixture was quenched with sat. ammonium chloride
extractionextracted with EA
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel flash chromatography (PE:EA=8:1)

Sources & evidence

ORD record: ord-9c2ad9f5bb4741e2b2b497d0414de4cd
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933113B2

Reaction notes

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