HCID 57910785, compound → HCID 24758850, compound

HRID 1644877Notes

Reaction equation

HRID 1644877 reaction equation
[CH3:1][Mg]Br.[CH3:4][C:5]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:34]=[N:33][C:32]([C:35](=[O:37])[CH3:36])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1)([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:11][N:10]=1)[CH:6]([CH3:8])[CH3:7]>C1COCC1.C1(C)C=CC=CC=1.C1COCC1.C(OCC)C>[CH3:4][C:5]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:34]=[N:33][C:32]([C:35]([OH:37])([CH3:1])[CH3:36])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1)([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:11][N:10]=1)[CH:6]([CH3:8])[CH3:7]

Participants

6

Reactant 2

HCID 57910785HCID 57910785, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 24758850HCID 24758850, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

Methyl magnesium bromide (30.9 mL of a 1.4 M solution in THF:toluene (25:75)) was added to a stirred solution of 7c (14.0 g, 30.9 mmol) in a mixture of THF (130 mL) and diethyl ether (260 mL) at 0° C. After approximately 1 h at 0° C., the reaction was quenched by the addition of saturated aqueous ammonium chloride, and the resulting mixture stirred for 15 min. The organic phase was separated, and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine, dried (magnesium sulfate) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-100% acetone/DCM as eluent) to furnish the title compound 7d. m/z (ES) 470 (MH)+. 1HNMR (500 MHz, CDCl3): δ 9.01 (d, 1H, J=9.1 Hz), 8.88 (d, 2H, J=5.0 Hz), 8.73 (d, 1H, J=9.2 Hz), 8.52 (d, 1H, J=2.7 Hz), 8.34 (dd, 1H, J=3.0, 9.4 Hz), 8.25 (d, 2H, J=8.5 Hz), 8.17 (d, 1H, J=9.1 Hz), 7.65 (d, 2H, J=8.5 Hz), 7.53 (t, 1H, J=5.0 Hz), 5.62 (s, 2H), 3.05 (m, 1H, J=6.7 Hz), 1.91 (s, 3H), 1.75 (s, 6H), 1.00 (d, 3H, J=6.6 Hz), 0.96 (d, 3H, J=6.4 Hz).

Workup

  1. customthe reaction was quenched by the addition of saturated aqueous ammonium chloride
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-100% acetone/DCM as eluent)

Sources & evidence

ORD record
ord-7168ecaf6ad3416bbe2042323bab71a3
Source dataset
uspto-grants-2012_02
Patent number
US08124628B2

Reaction notes

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