Sodium hydride → HCID 54579457, compound

HRID 1627563Notes

Reaction equation

[O:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[CH2:2]1.[CH3:16][C:17]1([CH3:29])[C:21]([CH3:23])([CH3:22])[O:20][B:19]([C:24]2[CH:25]=[N:26][NH:27][CH:28]=2)[O:18]1.[H-].[Na+]>CN(C=O)C>[OH:1][C:3]1([CH2:2][N:27]2[CH:28]=[C:24]([B:19]3[O:18][C:17]([CH3:29])([CH3:16])[C:21]([CH3:23])([CH3:22])[O:20]3)[CH:25]=[N:26]2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 90 °C

Procedure

A reaction mixture of compound (3-2) (214 mg; 1.0 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (3-3, 194 mg; 1.0 mmol) with NaH 60% dispersion in mineral oil (60 mg; 1.5 mmol) in 3 mL of DMF was stirred at 90° C. for 3 hours. The reaction mixture was partitioned between EtOAc (200 mL) and saturated NaHCO3 solution (50 mL) and brine (50 mL). The organic layer was dried (Na2SO4) and concentrated by vacuum to give 361 mg of (3-4) as a yellow grease (89% yield). 1H NMR (400 MHz, chloroform-D) δ ppm 1.21-1.34 (m, 12H) 1.39-1.50 (m, 9H) 1.56-1.78 (m, 4H) 3.14 (s, 2H) 3.72-3.91 (m, J=32.34 Hz, 2H) 4.05 (s, 2H) 7.65 (s, 1H) 7.80 (s, 1H) 8.00 (s, 1H). LCMS calcd for C20H34BN3O5 (M+H) 408, found 408. HPLC purity 85%.

Workup

customThe reaction mixture was partitioned between EtOAc (200 mL) and saturated NaHCO3 solution (50 mL) and brine (50 mL)
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated by vacuum

Sources & evidence

ORD record: ord-e4125927cac94443b74a7cbf99fe6f92
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785632B2

Reaction notes

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