HCID 117728727, compound → HCID 117728291, compound

HRID 718682Notes

Reaction equation

HRID 718682 reaction equation
CON(C)[C:4](=[O:38])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]3[N:16]=[CH:17][CH:18]=[C:19]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:14]3=[N:13][C:12]=2[C:26]#[C:27][C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]=2)=[CH:7][CH:6]=1.[CH3:40][Mg]Br>C1COCC1>[O:23]1[CH2:22][CH2:21][N:20]([C:19]2[C:14]3[N:15]([C:11]([C:8]4[CH:7]=[CH:6][C:5]([C:4](=[O:38])[CH3:40])=[CH:10][CH:9]=4)=[C:12]([C:26]#[C:27][C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]=4)[N:13]=3)[N:16]=[CH:17][CH:18]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 117728727HCID 117728727, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 117728291HCID 117728291, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of compound 65a (140 mg, 0.270 mmol) in 10 mL of THF at 0° C. was added methylmagnesium bromide (0.270 mL, 0.810 mmol, 3.0 M in Et2O) dropwise under an Argon atmosphere. After stirring at 0° C. for 1 h, the reaction was quenched with 2 mL of saturated NH4Cl. The mixture was treated with 50 mL of EtOAc and washed with water (25 mL), brine (25 mL) and then dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel (0:1-1:4 EtOAc/DCM) to afford the title compound 159 as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ=8.09-8.22 (m, 2H), 8.00 (s, 1H), 7.77-7.93 (m, 3H), 7.44-7.59 (m, 2H), 6.43 (d, J=5.6 Hz, 1H), 5.99 (d, J=6.1 Hz, 2H), 5.81 (s, 1H), 5.71 (s, 1H), 4.06 (br. s., 4H), 3.99 (s, 3H), 3.86 ppm (br. s., 4H). Mass spectrum (ESI, m/z): Calcd. for C29H25N5O4, 508.2 (M+H). found 508.5.

Workup

  1. customthe reaction was quenched with 2 mL of saturated NH4Cl
  2. additionThe mixture was treated with 50 mL of EtOAc
  3. washwashed with water (25 mL), brine (25 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel (0:1-1:4 EtOAc/DCM)

Sources & evidence

ORD record
ord-73dc11ba445547f2b3231c51f19a8027
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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