tert-Butyl 4-(5-cyanobenzo[d]oxazole-2-carbonyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate → tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-hydroxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174078Notes

Reaction equation

HRID 2174078 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([C:13]3[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[C:18]4[C:14]=3[CH:15]=[CH:16][N:17]4[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:12])=[N:8][C:7]=2[CH:32]=1)#[N:2].[CH3:33][Mg]Cl>C1COCC1>[C:28]([O:27][C:25]([N:17]1[C:18]2[C:14](=[C:13]([C:11]([C:9]3[O:10][C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:32][C:7]=4[N:8]=3)([OH:12])[CH3:33])[C:21]([O:22][CH3:23])=[CH:20][C:19]=2[CH3:24])[CH:15]=[CH:16]1)=[O:26])([CH3:29])([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 86701711tert-Butyl 4-(5-cyanobenzo[d]oxazole-2-carbonyl)-5-methoxy-7-methyl-1H-indole-1-carboxylateHCID 178418332HCID 178418332, compound

Product 1

HCID 86701712tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-hydroxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl 4-(5-cyanobenzo[d]oxazole-2-carbonyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (600 mg, 1.39 mmol) in THF (14 mL) at 0° C. methylmagnesium chloride, 3M in THF (1.39 mL, 4.17 mmol) was added. The reaction mixture was stirred for 15 min and then quenched with a saturated aq. solution of NH4Cl at 0° C. The layers were separated and the aqueous layer was extracted with EtOAc. The organic phase was dried over MgSO4 filtered and concentrated. The resulting residue was absorbed onto silica and purified by flash chromatography (0-50% EtOAc:heptanes) to give the title compound. MS (ESI+) m/z 448.22 (M+H).

Workup

  1. customquenched with a saturated aq. solution of NH4Cl at 0° C
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was absorbed onto silica
  8. custompurified by flash chromatography (0-50% EtOAc:heptanes)

Sources & evidence

ORD record
ord-ba9fa51435ab4589a8d0ca90b85cb36f
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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