HCID 57910774, compound → HCID 24758737, compound

HRID 1968664Notes

Reaction equation

HRID 1968664 reaction equation
C[Mg]Br.[CH3:4][C:5]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:33][N:32]=[C:31](C(OCC)=O)[CH:30]=2)=[CH:25][CH:24]=1)([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:11][N:10]=1)[CH:6]([CH3:8])[CH3:7]>C1(C)C=CC=CC=1.C1COCC1.C1COCC1>[CH3:4][C:5]([C:23]1[CH:24]=[CH:25][C:26]([C:29]2[O:33][N:32]=[C:31]([C:12]([OH:15])([CH3:13])[CH3:11])[CH:30]=2)=[CH:27][CH:28]=1)([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:11][N:10]=1)[CH:6]([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 57910774HCID 57910774, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 24758737HCID 24758737, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

Methyl magnesium bromide (334 μL of a 1.4M solution in toluene:THF (75:25), 0.468 mmol) was added to a stirred solution of 1c (55.0 mg, 0.117 mmol) in THF (1.00 mL) at 0° C. After approximately 1 h, the reaction was quenched with water, and the resulting mixture was purified directly by flash chromatography on silica gel (gradient elution; 0%-100% EtOAc/hexanes as eluent) to afford the title compound 2a. m/z (ES) 457 (MH)+. 1HNMR (500 MHz, CDCl3): δ 8.61 (d, 1H, J=4.6 Hz), 7.67 (m, 1H), 7.67 (d, 2H, J=8.5 Hz), 7.58 (d, 1H, J=8.0 Hz), 7.36 (d, 2H, J=8.5 Hz), 7.25 (m, 1H), 7.19 (d, 2H, J=8.3 Hz), 6.92 (d, 2H, J=8.9 Hz), 5.22 (s, 2H), 2.72 (m, 1H), 1.68 (s, 6H), 1.63 (s, 3H), 0.89 (d, 3H, J=6.7 Hz), 0.86 (d, 3H, J=6.7 Hz).

Workup

  1. customthe reaction was quenched with water
  2. customthe resulting mixture was purified directly by flash chromatography on silica gel (gradient elution; 0%-100% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-60b12ee7cee74bfe9e8151da9c1dd518
Source dataset
uspto-grants-2013_04
Patent number
US08426413B2

Reaction notes

Loading…