Tetrahydrofuran → HCID 71571667, compound

HRID 1777785Notes

Reaction equation

HRID 1777785 reaction equation
[C:1]([C:4]1[N:9]2[C:10](=[O:25])[N:11]([CH2:13][CH2:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=3)[N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([Mg]Br)=[CH:30][CH:29]=1.[CH2:36]1COCC1>>[OH:3][C:1]([C:4]1[N:9]2[C:10](=[O:25])[N:11]([CH2:13][CH2:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=3)[N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1)([CH3:36])[CH2:2][C:31]1[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 89584620HCID 89584620, compoundHCID 178491912HCID 178491912, compound

Product 1

HCID 71571667HCID 71571667, compoundYield 26%

Conditions

Temperature
-78 °C

Procedure

In a flame-dried, 5 mL microwave vial was placed 7-1 (20 mg, 0.054 mmol) in THF (0.54 mL) under dry N2 gas. The reaction mixture was cooled to −78° C., and a 0.5 M solution of (4-methoxyphenyl)magnesium bromide in THF (0.119 mmol, 0.24 mL) was added. After stirring for 15 min, the reaction was quenched with sat. aq. NH4Cl (0.25 mL) and diluted with CH2Cl2 (2 mL). The mixture was transferred to a phase separator column, and the organic layer was collected and dried under a stream of N2 gas. The crude product was purified by reversed phase HPLC (eluting with 20-60% acetonitrile/water with 0.1% NH4OH modifier). Pure fractions were pooled and dried to give 6.3 mg (26%) of 7-2. HRMS (ES) 441.1911 found (M+H) found, 441.1923 required.

Workup

  1. customthe reaction was quenched with sat. aq. NH4Cl (0.25 mL)
  2. additiondiluted with CH2Cl2 (2 mL)
  3. customthe organic layer was collected
  4. dry with materialdried under a stream of N2 gas
  5. customThe crude product was purified by reversed phase HPLC (eluting with 20-60% acetonitrile/water with 0.1% NH4OH modifier)
  6. customdried

Sources & evidence

ORD record
ord-c92bedac79954a14bde16f90c03cefd1
Source dataset
uspto-grants-2016_02
Patent number
US09266881B2

Reaction notes

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