HCID 66919431, compound → HCID 66919361, compound

HRID 1364509Notes

Reaction equation

HRID 1364509 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[CH:18]=[CH:17][C:16]([C:21](=[O:30])[CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)([CH3:20])[CH2:15][C:14]=3[CH:13]=[N:12]2)=[CH:7][CH:6]=1>C1COCC1>[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[CH:18]=[CH:17][C:16]([C:21]([OH:30])([CH2:22][CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH3:1])([CH3:20])[CH2:15][C:14]=3[CH:13]=[N:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 66919431HCID 66919431, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 66919361HCID 66919361, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 3 M THF solution of methylmagnesium bromide (0.15 mL, 5.4 eq) was added to a THF (1 mL) solution of Example 202 (30 mg, 0.083 mmol) at room temperature. After 2.5 h, the reaction was quenched with saturated NH4Cl and extracted with EtOAc. The EtOAc layer was concentrated and purified by flash column chromatography (4 g ISCO silica gel cartridge, 0 to 50% EtOAc-hexanes) to give the title compound (25.7 mg, 82%) as a 1:1 mixture of two isomers. MS found: (M+H)+=377.

Workup

  1. customthe reaction was quenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. concentrationThe EtOAc layer was concentrated
  4. custompurified by flash column chromatography (4 g ISCO silica gel cartridge, 0 to 50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-5f0318d354ff412bb8e5cf4291511b61
Source dataset
uspto-grants-2011_02
Patent number
US07888381B2

Reaction notes

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