Triphenylphosphine → 1-Benzyl-3-(bromomethyl)-1H-indazole

HRID 343096Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[CH2:22]([N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH2:38]O)=[N:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[CH2:22]([N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH2:38][Br:20])=[N:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 550 mg (2.09 mmol, 1.3 equiv) of triphenylphosphine in 10 mL of acetonitrile at 0° C. is added 0.1 mL (1.93 mmol, 1.2 equiv) of Br2. The resulting orange-yellow suspension is stirred 10 min at 0° C., then a solution of 383 mg (1.61 mmol) of (1-Benzyl-1H-indazol-3-yl) methanol, prepared as in Intermediate 15, in 5 mL of acetonitrile is added over 2 min. The resulting solution is stirred 1 h at RT, and the solvent is removed in vacuo. Purification of the residue by silica gel flash column chromatography using hexane/EtOAc 5/1 as eluent afforded 305 mg of the title compound as a white solid: 1H NMR (CDCl3, 300 MHz) δ7.82 (d, 1H), 7.40-7.16 (m, 8H), 5.59 (s, 2H), 4.90 (s, 2H); Rf =0.75 in hexane/EtOAc 2/1.

Workup

stirringThe resulting solution is stirred 1 h at RT
customthe solvent is removed in vacuo
customPurification of the residue by silica gel flash column chromatography

Sources & evidence

ORD record: ord-b11dab2b4fd041c8b78aeb683b326d01
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859007

Reaction notes

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