Methyl chloroformate → HCID 70562147, compound

HRID 1477890Notes

Reaction equation

HRID 1477890 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([N:22]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)([CH2:11][CH3:12])[C:9]#[CH:10])=[CH:4][CH:3]=1.[Li]CCCC.[C:40](Cl)(=[O:43])[O:41][CH3:42]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([N:22]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)([CH2:11][CH3:12])[C:9]#[C:10][C:40]([O:41][CH3:42])=[O:43])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 86705050HCID 86705050, compoundHCID 178418339Butyllithium

Product 1

HCID 70562147HCID 70562147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound N-(1-(3-(4-chlorophenyl)pent-1-yn-3-yl)-1H-indol-4-yl)-N-((2-(trimethylsilyl)ethoxy)methyl)methanesulfonamide (2.9 g, 5.6 mmol, enantiomer A), as described in Example 55 Step A, in dry THF (10 mL) was added BuLi (4.5 mL, 11.2 mmol, 2.5 M in hexane) at −78° C. After stirring for 30 min, methyl carbonchloridate (0.88 mL, 6.2 mmol) was added to the mixture at −78° C. The resulting mixture was stirred for another 2 h and then quenched with saturated NH4Cl (10 mL), extracted with ethyl acetate, washed with brine (50 mL), dried over sodium sulfate, then filtered. After removing the organic solvent, the residue was purified by column chromatography (EA/PE=1:10) to obtain the title compound. LC/MS m/z=597.0 [M+Na]+.

Workup

  1. stirringThe resulting mixture was stirred for another 2 h
  2. customquenched with saturated NH4Cl (10 mL)
  3. extractionextracted with ethyl acetate
  4. washwashed with brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customAfter removing the organic solvent
  8. customthe residue was purified by column chromatography (EA/PE=1:10)

Sources & evidence

ORD record
ord-ab118bf8717641c2834e85a1507d6fa4
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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