Chlorosuccinimide → 2-benzyl-3-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole

HRID 1973002Notes

Reaction equation

[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([B:17]3[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]3)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26]N1C(=O)CCC1=O>C1COCC1>[CH2:1]([N:8]1[C:16]([Cl:26])=[C:15]2[C:10]([CH:11]=[C:12]([B:17]3[O:18][C:19]([CH3:25])([CH3:24])[C:20]([CH3:23])([CH3:22])[O:21]3)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-Indazole (200 mg, 0.598 mmol) in THF (2 mL), was added N-chlorosuccinimide (95.9 mg, 0.718 mmol). The mixture was heated at 40° C. for 4 hr, cooled to rt then concentrated to dryness. The crude material was purified by ISCO® chromatography using a gradient of 1-7% EtOAc in hexane to afford the desired product (180.1 mg, 82%). 1H NMR (400 MHz, DMF-d6) δ 7.98 (s, 1H), 7.59 (d, 1H), 7.38-7.28 (m, 4H), 7.22-7.19 (m, 2H), 5.74 (s, 2H), 1.34 (s, 12H); LC-MS m/z [M+H]+ 369.2, RT 3.94 min.

Workup

temperaturecooled to rt
concentrationthen concentrated to dryness
customThe crude material was purified by ISCO® chromatography

Sources & evidence

ORD record: ord-51785f317a1e428fb50b0696f9b564f3
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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