Boron tribromide → HCID 46931462, compound

HRID 452309Notes

Reaction equation

[F:1][C:2]1[CH:9]=[C:8]([C:10]#[C:11][C:12]2[S:13][C:14]3[CH:20]=[C:19]([O:21]C)[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH:7]=[CH:6][C:3]=1[NH:4][CH3:5].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:9]=[C:8]([C:10]#[C:11][C:12]2[S:13][C:14]3[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH:7]=[CH:6][C:3]=1[NH:4][CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 25 mL round bottomed flask equipped with a magnetic stir bar containing DCM (5.2 mL) was placed 8 (0.08 g, 0.26 mmol). The reaction mixture was cooled to 0° C. and BBr3 (0.75 mL of 1M in DCM) was added drop wise. The reaction was stirred at RT for 8 hr. The reaction was then neutralized with sat. NaHCO3 and extracted into DCM (2×10 mL). The combined organic extracts were washed with water (10 mL), brine (10 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified over silica gel using EtOAc:Hexanes (1:3) as the eluent to afford W366 (0.02 g, 26%) as a brown solid. 1H NMR (400 MHz, DMSO-d6), δ: 2.5 (d, J=10.4 Hz, 3H), 6.06-6.08 (m, 1H), 6.42 (t, J=8.8 Hz, 1H), 6.74 (dd, J=8.8, 2.4 Hz, 1H), 7.05-7.14 (m, 2H), 7.54 (d, J=8.8, 1H), 9.76 (br s, 1H); MS (ESI): 299.0 (M+H+).

Workup

customTo a 25 mL round bottomed flask equipped with a magnetic stir bar
extractionextracted into DCM (2×10 mL)
washThe combined organic extracts were washed with water (10 mL), brine (10 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified over silica gel
customto afford W366 (0.02 g, 26%) as a brown solid

Sources & evidence

ORD record: ord-f3d5540546084a04bff4c846abcde643
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08491869B2

Reaction notes

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