Boron tribromide → HCID 136253070, compound

HRID 1027230Notes

Reaction equation

C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([OH:20])=[C:16]2[Cl:19])=[CH:11][C:10]=1[C:21]1[N:22]=[N:23][C:24]([N:27]([CH3:38])[CH:28]2[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][C:30]([CH3:37])([CH3:36])[CH2:29]2)=[CH:25][CH:26]=1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:19][C:16]1[C:17]2[C:12](=[CH:11][C:10]([C:21]3[N:22]=[N:23][C:24]([N:27]([CH3:38])[CH:28]4[CH2:29][C:30]([CH3:36])([CH3:37])[NH:31][C:32]([CH3:35])([CH3:34])[CH2:33]4)=[CH:25][CH:26]=3)=[C:9]([OH:8])[CH:18]=2)[CH:13]=[CH:14][C:15]=1[OH:20]

Participants

Conditions

Temperature: -78 °C

Procedure

To a mixture of 7-(benzyloxy)-1-chloro-6-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)naphthalen-2-ol (25 mg, 0.047 mmol) in DCM (1 mL) was added BBr3 (1 M solution in DCM, 0.25 mL, 0.25 mmol) slowly at −78° C. The mixture was stirred at −78° C. for 10 minutes, then warmed to RT and stirred for 1.5 h. The reaction was quenched with MeOH and concentrated. The residue was loaded onto a 1 g SCX column, washed with MeOH and eluted with 2 M NH3 in MeOH. The product-containing fractions were concentrated to give the desired product as a light brown solid (10 mg, 48.2% yield). LCMS Rt=0.54 min [Method Q], MS (M+1)=441.3. 1H NMR (METHANOL-d4) δ 8.17-8.27 (m, 2H), 7.66 (d, J=9.1 Hz, 1H), 7.46 (s, 1H), 7.32 (d, J=10.1 Hz, 1H), 7.00 (d, J=9.1 Hz, 1H), 5.13 (t, J=11.9 Hz, 1H), 3.02 (s, 3H), 1.71-1.79 (m, 2H), 1.59-1.68 (m, 2H), 1.44 (s, 6H), 1.28 (s, 6H).

Workup

temperaturewarmed to RT
stirringstirred for 1.5 h
customThe reaction was quenched with MeOH
concentrationconcentrated
washwashed with MeOH
washeluted with 2 M NH3 in MeOH
concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record: ord-cdbcc7e6a4df4b2d8e097a4cc9cb35b6
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729263B2

Reaction notes

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