Ethyl chloroformate → HCID 86728308, compound

HRID 1776930Notes

Reaction equation

HRID 1776930 reaction equation
[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:39]([CH3:44])[S:40]([CH3:43])(=[O:42])=[O:41])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=7)=[C:24]([C:34]([NH:36][CH3:37])=[O:35])[C:23]=6[CH:38]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1.C([Li])CCC.Cl[C:51]([O:53][CH2:54][CH3:55])=[O:52]>C1COCC1>[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:39]([CH3:44])[S:40]([CH3:43])(=[O:42])=[O:41])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=7)=[C:24]([C:34]([N:36]([CH3:37])[C:51](=[O:52])[O:53][CH2:54][CH3:55])=[O:35])[C:23]=6[CH:38]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 715091141426960-33-9HCID 178418339Butyllithium

Product 1

HCID 86728308HCID 86728308, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (100 mg, 0.163 mmol) in THF (2 mL) at −78° C. under N2 added n-butyllithium (0.203 ml, 0.325 mmol). After 10 mins, ethyl chloroformate (61.8 mg, 0.569 mmol) was added to the reaction mixture. And the reaction mixture was warmed to room temperature and stirred overnight under N2. The reaction mixture was quenched with 5 ml water extracted with 3×10 mL ethyl acetate. The organic layers were combined, washed with 2×5 mL of saturated brine, dried over anhydrous sodium sulfate and concentrated under vacuum. Silica gel chromatography eluted with ethyl acetate/hexane (20-100%) resulted in 38 mg (34%) of Ethyl (5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-6-(N-methylmethylsulfonamido)benzofuran -3-carbonyl)(methyl)carbamate (Compound 208) as a white solid. LC-MS (ES, m/z) C35H28F2N4O7S: 686. Found: 687 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with 5 ml water
  2. extractionextracted with 3×10 mL ethyl acetate
  3. washwashed with 2×5 mL of saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. washSilica gel chromatography eluted with ethyl acetate/hexane (20-100%)

Sources & evidence

ORD record
ord-7bc8a21634a548bc9170b3057297df92
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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