Boron tribromide → HCID 59752536, compound

HRID 2106279Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-(4-chloro-phenyl)-1-(3-methoxy-benzyl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene (Example 105, 0.1 mmol) in CH2Cl2 (5 mL) was cooled to 0° C., and 1 M BBr3 in CH2Cl2 (0.5 mL) was added. The mixture was allowed to warm to 25° C. After 2 h, satd. aq. NaHCO3 (5 mL) was added. The layers were separated, and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organic layers were dried over Na2SO4 and concentrated. Purification by flash chromatography (2 M NH3 in MeOH/CH2Cl2) provided the title compound (10 mg). MS (ESI): exact mass calculated for C20H20ClN3O, 353.13; found, m/z 354.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.40-7.38 (m, 2H), 7.35-7.32 (m, 2H), 7.03 (t, J=7.9 Hz, 1H), 6.57 (dd, J=8.1, 2.0 Hz, 1H), 6.49 (d, J=8.1 Hz, 1H), 6.39-6.37 (br m, 1H), 5.20 (s, 2H), 2.81-2.78 (br m, 4H), 2.74-2.72 (br m, 2H), 2.70-2.68 (br m, 2H).

Workup

customThe layers were separated
extractionthe aqueous layer was extracted with EtOAc (2×5 mL)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated
customPurification by flash chromatography (2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-57d7ebbc44914b87a0b083c45ce7bc6a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579470B2

Reaction notes

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