Carbon tetrabromide → 5-(Bromomethyl)-7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole

HRID 913797Notes

Reaction equation

HRID 913797 reaction equation
[CH3:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:9]=2)[CH:5]=[C:4]([CH2:19]O)[CH:3]=1.C(Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.CCCCC>[Br:22][CH2:19][C:4]1[CH:3]=[C:2]([CH3:1])[C:10]2[C:6](=[CH:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:9]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57545931(7-Methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)methanol

Product 1

HCID 575462295-(Bromomethyl)-7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)methanol (138 mg, 0.472 mmol) and carbon tetrabromide (235 mg, 0.708 mmol) in tetrahydrofuran (1 mL) at 0° C. was added triphenylphosphine (186 mg, 0.708 mmol). The resulting solution was stirred at room temperature for 30 min. The reaction was diluted with several volumes of pentane and filtered to remove undissolved solids. The organics were concentrated and purified by column chromatography (5→12% EtOAc/Hex) to give 114 mg (68%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 8.03 (s, 1H), 7.48 (s, 1H), 7.06 (s, 1H), 5.68 (s, 2H), 4.55 (s, 2H), 3.61 (m, 2H), 2.59 (s, 3H), 0.91 (m, 2H), −0.05 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 148.8, 131.6, 129.0, 126.6, 123.3, 121.6, 118.1, 81.7, 67.3, 35.4, 17.7, 17.1, −1.5.

Workup

  1. filtrationfiltered
  2. customto remove undissolved solids
  3. concentrationThe organics were concentrated
  4. custompurified by column chromatography (5→12% EtOAc/Hex)
  5. customto give 114 mg (68%) as a colorless oil

Sources & evidence

ORD record
ord-abf9e5cc51ef4746a78831106b2b134c
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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