Boron tribromide → HCID 73855121, compound

HRID 2121963Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[N:12]=[C:13]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=2)[C:16](=[O:27])[C:15](=[C:28]2[N:32]([CH3:33])[C:31]3[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=3[S:29]2)[S:14]1)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([NH:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[N:12]=[C:13]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)[C:16](=[O:27])[C:15](=[C:28]2[N:32]([CH3:33])[C:31]3[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=3[S:29]2)[S:14]1)[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a N2-purged flask was added the product of Example 114 (60 mg, 0.11 mmol) and anhydrous DCM (5 mL). The solution was cooled to −78° C. prior to the addition of a 1.0M solution of BBr3 in DCM (0.50 mL). The solution was allowed to warm to ambient temperature with stirring. After 7 h the solution was quenched by addition of MeOH (10 mL) and then concentrated under reduced pressure. The crude material was purified by reverse-phase HPLC (C18 column), eluting with 0.05% TFA in MeCN—H2O (1:9 to 9:1) to provide the title compound (15 mg, 26%). 1H-NMR (CDCl3): δ 7.40 (1H, d), 7.35 (1H, t), 7.29 (1H, dd), 7.13-7.25 (3H, m), 6.95-7.01 (3H, m), 6.76 (1H, dd), 6.49 (1H, d), 5.08 (2H, s), 3.56 (3H, s), 3.02 (2H, q), 1.05 (3H, t); MS(ESI): 514 (MH+).

Workup

customTo a N2-purged flask
temperatureto warm to ambient temperature
customAfter 7 h the solution was quenched by addition of MeOH (10 mL)
concentrationconcentrated under reduced pressure
customThe crude material was purified by reverse-phase HPLC (C18 column)
washeluting with 0.05% TFA in MeCN—H2O (1:9 to 9:1)

Sources & evidence

ORD record: ord-4806e7b16758436ba17c7d9afbbd78f0
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696473B2

Reaction notes

Loading…